Name: 2127-09-5|2-Mercapto-5-nitropyridine|98%
Brand: Ambeed
SKU: A817152
Rating: 99 (25 reviews)

1
[ 4548-45-2 ]
[ 2127-09-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	With thiourea In ethanol for 12h; Reflux;	7.a 2-mercapto-5-nitropyridine A mixture of 2-chloro-5-nitro-pyridine(2g, 12.6mmol) and thiourea (lg, 13.1mmol) were dissolved in absolute ethanol (30ml) and refluxed for 12h. The reaction mixture was yellow and precipitated solid . After cooling to room temperature, the precipitate was filtered off and dried. The solid was suspended in water (15 ml). A solution of NaOH (10 ml) was added dropwise at room temperature with stirring. After stirring for 30 min, the insoluble matter was filtered off. The filtrate was acidified with dilute hydrochloric acid and stirred for 30 min. The filter cake was washed with water and dried to give the title compound (1.1 g, 50%).
	With methanol; potassium hydrosulfide
	With sodium sulfide; ethanol; water

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Shanghai Institute of Materia Medica (in: CAS); SHIONOGI & CO., LTD. - CN103626693, 2016, B Location in patent: Paragraph 0174-0176
[2]Phillips; Shapiro [Journal of the Chemical Society, 1942, p. 584] Binz; Maier-Bode [Angewandte Chemie, 1936, vol. 49, p. 486,488] Colonna [Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1941, vol. 2, p. 145] Takahashi; Saikati [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1942, vol. 62, p. 140,142; dtsch. Ref. S. 44, 45][Chem.Abstr., 1951, p. 1592] Raeth [Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 105,115] Plazek [Roczniki Chemii, 1937, vol. 17, p. 97][Chemisches Zentralblatt, 1937, vol. 108, # II, p. 73]
[3]Current Patent Assignee: NORTHROP GRUMMAN CORPORATION - US2476655, 1941, A

2
[ 2127-09-5 ]
[ 106-95-6 ]
2-allylmercapto-5-nitro-pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol
	With potassium carbonate In acetone at 20℃;

Reference： [1]Semonsky; Cerny [Collection of Czechoslovak Chemical Communications, 1955, vol. 20, p. 1221,1224, 1226]
[2]Markovic, Tim; Murray, Philip R.D.; Rocke, Benjamin N.; Shavnya, Andre; Blakemore, David C.; Willis, Michael C. [Journal of the American Chemical Society, 2018, vol. 140, # 46, p. 15916 - 15923]

3
[ 2127-09-5 ]
[ 79-11-8 ]
(5-nitro-[2]pyridylmercapto)-acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With water
	With ethanol

Reference： [1]Takahashi; Goto [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1943, vol. 63, p. 425][Chem.Abstr., 1951, p. 4717] Surrey; Lindwall [Journal of the American Chemical Society, 1940, vol. 62, p. 1697,1698]
[2]Semonsky; Cerny [Collection of Czechoslovak Chemical Communications, 1955, vol. 20, p. 1221,1224, 1226]

4
[ 2127-09-5 ]
[ 74-88-4 ]
[ 20885-21-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With monosodium carbonate In ethanol; water at 20℃; for 1h;	1 Preparation of 3-Nitro-6-(methylthio)pyridine From 2-Mercapto-5-Nitropyridine. Preparation of 3-Nitro-6-(methylthio)pyridine From 2-Mercapto-5-Nitropyridine. 2-Mercapto-5-nitro pyridine (20.0 g, 128 mmol) was suspended in H2O/ethanol (43 mL/13 mL). Sodium carbonate monohydrate (17.49 g, 141 mmol, dissolved in 86 mL of H2O) was added to the above slurry dropwise. Methyl iodide (20.0 g, 141 mmol) was added to the above mixture and the mixture was stirred at rt for 1 h. The solid was filtered and washed with water and ethanol to provide the title compound in quantitative yield.
	With methanol

Reference： [1]Current Patent Assignee: PFIZER INC - US6649636, 2003, B1 Location in patent: Page/Page column 52
[2]Takahashi et al. [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 1447][Chem.Abstr., 1959, p. 8133] Takahashi; Saikati [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1942, vol. 62, p. 140,142; dtsch. Ref. S. 44, 45][Chem.Abstr., 1951, p. 1592]

5
[ 2127-09-5 ]
[ 27885-56-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With water; tin(ll) chloride
	With hydrogenchloride; tin(ll) chloride

Reference： [1]Delarge; Thunus; Beckers; et al. [European Journal of Medicinal Chemistry, 1984, vol. 19, # 6, p. 559 - 565]
[2]Raeth [Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 105,115]

6
[ 2127-09-5 ]
[ 27885-57-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium dithionite Erwaermen des Reaktionsgemisches mit Acetanhydrid;

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]

7
[ 2127-09-5 ]
[ 130156-01-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrachloromethane; chlorine
	With thionyl chloride In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;

Reference： [1]Current Patent Assignee: NORTHROP GRUMMAN CORPORATION - US2476655, 1941, A
[2]He, Lei; Wang, Liangliang; Wang, Zhisong; Li, Tiantian; Chen, Hui; Zhang, Yaning; Hu, Zeping; Dimitrov, Dimiter S.; Du, Juanjuan; Liao, Xuebin [Journal of Medicinal Chemistry, 2021, vol. 64, # 21, p. 15716 - 15726]

8
[ 2127-09-5 ]
[ 174485-82-6 ]

Yield	Reaction Conditions	Operation in experiment
47%	With hydrogenchloride; water; chlorine; acetic acid Cooling;	1.E131 To an ice-cold solution of 5-nitro-pyridine-2-thiol (1.27 g, 8.13 mmol) in 1N aqueous HCl (25 mL) and acetic acid (5 mL) was vigorously bubbled chlorine (gas) for 15 min, followed by nitrogen for 5 min. the solid was collected by filtration, washed with cold 1N aqueous HCl and water and dried in vacuo: yield 842 mg (47%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.60 (d, J=2.0 Hz, 1H), 8.84 (dd, J=8.6, 2.3 Hz, 1H), 8.35 (d, J=8.6 Hz, 1H).
	With hydrogenchloride; chlorine

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2010/256092, 2010, A1 Location in patent: Page/Page column 137
[2]Caldwell et al. [Journal of the American Chemical Society, 1944, vol. 66, p. 1479,1482]

9
[ 2127-09-5 ]
[ 2127-10-8 ]

Yield	Reaction Conditions	Operation in experiment
	With water; dihydrogen peroxide
2.668 g	Stage #1: 2-mercapto-5-nitropyridine With sodium hydroxide In water for 0.5h; Inert atmosphere; Stage #2: With potassium hexacyanoferrate(III) In water at 20℃; Inert atmosphere;
	Stage #1: 2-mercapto-5-nitropyridine With sodium hydroxide In water for 0.5h; Inert atmosphere; Stage #2: With potassium hexacyanoferrate(III) In water at 20℃; for 12h; Inert atmosphere;

Reference： [1]Raeth [Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 105,115]
[2]Cui, Benqiang; Kosobokov, Mikhail; Matsuzaki, Kohei; Tokunaga, Etsuko; Shibata, Norio [Chemical Communications, 2017, vol. 53, # 44, p. 5997 - 6000]
[3]Cui, Benqiang; Jia, Shichong; Tokunaga, Etsuko; Saito, Norimichi; Shibata, Norio [Chemical Communications, 2017, vol. 53, # 95, p. 12738 - 12741]

10
[ 2127-09-5 ]
[ 108-24-7 ]
[ 27885-57-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: 2-mercapto-5-nitropyridine With sodium dithionite; water for 0.166667h; Cooling with ice; Stage #2: acetic anhydride In water for 2h; Cooling with ice;	Intermediate 39--5-Acetylamino-2-pyridinesulfonyl chloride 2-Mercapto-5-nitropyridine (1 g, 6.40 mmol) was dissolved in water, and sodium dithionite (3.9 g, 22.4 mmol) was added in an ice bath, and stirred for 10 minutes. Acetic anhydride (850 μL, 8.97 mmol) was added dropwise, and the mixture was reacted for 2 hours in an ice bath, filtered, and the filter cake was washed with ice water and dried at 50 ° C overnight. Intermediate 39a (yellow solid, 602 mg). The yield was 56%.
50%	With sodium dithionite In water at 0℃; for 2h;	1 4.1.1 2-Thiol-5-acetaminopyridine (1) 2-Mercapto-5-nitropyridine (Bionet Research) (10 g, 64 mmol) was suspended in 100 mL of water and sodium hydrosulfite (39 g, 224 mmol) was added with stirring at 0°C. Acetic anhydride (8.4 mL, 89.6 mmol) was then added. The mixture was stirred for 2 h, always kept in ice, and the yellow precipitate was filtered, washed with water, and dried to give 1 as a bright yellow solid (5.4g, 50% yield). 1H NMR (DMSO-d6) δ: 2.01 (s, 3H); 7.22-7.36 (m, 2H); 8.22 (s, 1H); 10.07 (s, 1H).
45%	With sodium disulfite

Reference： [1]Current Patent Assignee: Shanghai Institute of Materia Medica (in: CAS); CHINESE ACADEMY OF SCIENCES - CN109651208, 2019, A Location in patent: Paragraph 0217-0219
[2]Bozdag, Murat; Ferraroni, Marta; Nuti, Elisa; Vullo, Daniela; Rossello, Armando; Carta, Fabrizio; Scozzafava, Andrea; Supuran, Claudiu T. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 334 - 340]
[3]Nimitz, Jonathan S. [Synthetic Communications, 1981, vol. 11, # 4, p. 273 - 280]

11
[ 4487-59-6 ]
[ 2127-09-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With trisodium thiophosphate In methanol Heating;

Reference： [1]Bieniarz; Cornwell [Tetrahedron Letters, 1993, vol. 34, # 6, p. 939 - 942]

Yield	Reaction Conditions	Operation in experiment
	With water; sodium carbonate
	With ammonia; water
	With sodium hydroxide; water

13
[ 67-56-1 ]
[ 650608-81-4 ]
[ 2127-09-5 ]
[ 709-50-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With citrate-phosphate buffer; almond β-D-glucosidase at 25℃; for 1h;

Reference： [1]Niemiec-Cyganek; Szeja [Polish Journal of Chemistry, 2003, vol. 77, # 8, p. 969 - 973]

14
[ 64-17-5 ]
[ 650608-81-4 ]
[ 2127-09-5 ]
(2R,3R,4S,5S,6R)-2-Ethoxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With citrate-phosphate buffer; almond β-D-glucosidase at 25℃; for 1h;

Reference： [1]Niemiec-Cyganek; Szeja [Polish Journal of Chemistry, 2003, vol. 77, # 8, p. 969 - 973]

15
[ 857665-53-3 ]
[ 2127-09-5 ]
[ 719-22-2 ]
methyl 2-methyl-2-[(5-nitropyridin-2-yl)sulfanyl]propionate [ No CAS ]
3,5-di-t-butyl-4-hydroxyphenyl diphenylphosphinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In chloroform at 20℃; for 12h;

Reference： [1]Ikegai, Kazuhiro; Pluempanupat, Wanchai; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 2006, vol. 79, # 5, p. 780 - 790]

16
[ 2127-09-5 ]
5-amino-pyridine-2-sulfonic acid-(5-cyano-[2]pyridylamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: chlorine; aqueous HCl / <10 2: pyridine 3: aqueous NaOH; Na₂S₂O₄

Reference： [1]Caldwell et al. [Journal of the American Chemical Society, 1944, vol. 66, p. 1479,1482]

17
[ 2127-09-5 ]
6-(5-amino-pyridine-2-sulfonylamino)-nicotinic acid amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: chlorine; aqueous HCl / <10 2: pyridine 3: aqueous NaOH; Na₂S₂O₄

Reference： [1]Caldwell et al. [Journal of the American Chemical Society, 1944, vol. 66, p. 1479,1482]

18
[ 2127-09-5 ]
2-(5-amino-pyridine-2-sulfonylamino)-nicotinic acid amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: chlorine; aqueous HCl / <10 2: pyridine 3: aqueous NaOH; Na₂S₂O₄

Reference： [1]Caldwell et al. [Journal of the American Chemical Society, 1944, vol. 66, p. 1479,1482]

19
[ 2127-09-5 ]
[ 861027-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: chlorine; aqueous HCl / <10 2: pyridine

Reference： [1]Caldwell et al. [Journal of the American Chemical Society, 1944, vol. 66, p. 1479,1482]

20
[ 2127-09-5 ]
[ 861045-34-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: chlorine; aqueous HCl / <10 2: pyridine

Reference： [1]Caldwell et al. [Journal of the American Chemical Society, 1944, vol. 66, p. 1479,1482]

21
[ 2127-09-5 ]
[ 861045-36-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: chlorine; aqueous HCl / <10 2: pyridine

Reference： [1]Caldwell et al. [Journal of the American Chemical Society, 1944, vol. 66, p. 1479,1482]

22
[ 2127-09-5 ]
[ 64356-57-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: aqueous Na₂S₂O₄ / Erwaermen des Reaktionsgemisches mit Acetanhydrid 2: aqueous HCl; chlorine 3: aqueous NH₃ 4: aqueous NaOH
	Multi-step reaction with 4 steps 1: sodium dithionite / water / 2 h / 0 °C 2: sulfuric acid; sodium hypochlorite / 1 h / 0 °C 3: ammonium hydroxide / acetonitrile / 0.5 h / 0 - 20 °C 4: hydrogenchloride / water; ethanol / 3 h / Inert atmosphere; Reflux

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]
[2]Bozdag, Murat; Ferraroni, Marta; Nuti, Elisa; Vullo, Daniela; Rossello, Armando; Carta, Fabrizio; Scozzafava, Andrea; Supuran, Claudiu T. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 334 - 340]

23
[ 2127-09-5 ]
[ 409112-27-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aqueous Na₂S₂O₄ / Erwaermen des Reaktionsgemisches mit Acetanhydrid 2: aqueous HCl; chlorine
	Multi-step reaction with 2 steps 1.1: sodium dithionite; water / 0.17 h / Cooling with ice 1.2: 2 h / Cooling with ice 2.1: sulfuric acid; sodium hypochlorite / 1 h / Cooling with ice

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]
[2]Current Patent Assignee: Shanghai Institute of Materia Medica (in: CAS); CHINESE ACADEMY OF SCIENCES - CN109651208, 2019, A

24
[ 2127-09-5 ]
5-acetylamino-pyridine-2-sulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aqueous Na₂S₂O₄ / Erwaermen des Reaktionsgemisches mit Acetanhydrid 2: acetic acid; aqueous H₂O₂

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]

25
[ 2127-09-5 ]
[ 98548-28-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: aqueous Na₂S₂O₄ / Erwaermen des Reaktionsgemisches mit Acetanhydrid 2: aqueous HCl; chlorine 3: aqueous NH₃
	Multi-step reaction with 3 steps 1: sodium dithionite / water / 2 h / 0 °C 2: sulfuric acid; sodium hypochlorite / 1 h / 0 °C 3: ammonium hydroxide / acetonitrile / 0.5 h / 0 - 20 °C

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]
[2]Bozdag, Murat; Ferraroni, Marta; Nuti, Elisa; Vullo, Daniela; Rossello, Armando; Carta, Fabrizio; Scozzafava, Andrea; Supuran, Claudiu T. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 334 - 340]

26
[ 2127-09-5 ]
(5-amino-pyridine-2-sulfonyl)-guanidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: aqueous Na₂S₂O₄ / Erwaermen des Reaktionsgemisches mit Acetanhydrid 2: aqueous HCl; chlorine 3: acetone; aqueous NaOH 4: aqueous HCl

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]

27
[ 2127-09-5 ]
5-amino-pyridine-2-sulfonic acid anilide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: aqueous Na₂S₂O₄ / Erwaermen des Reaktionsgemisches mit Acetanhydrid 2: aqueous HCl; chlorine 3: pyridine 4: aqueous NaOH

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]

28
[ 2127-09-5 ]
5-amino-pyridine-2-sulfonic acid-[2]pyridylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: aqueous Na₂S₂O₄ / Erwaermen des Reaktionsgemisches mit Acetanhydrid 2: aqueous HCl; chlorine 3: pyridine 4: aqueous NaOH

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]

29
[ 2127-09-5 ]
5-amino-pyridine-2-sulfonic acid thiazol-2-ylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: aqueous Na₂S₂O₄ / Erwaermen des Reaktionsgemisches mit Acetanhydrid 2: aqueous HCl; chlorine 4: aqueous NaOH

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]

30
[ 2127-09-5 ]
5-amino-pyridine-2-sulfonic acid pyrimidin-2-ylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: aqueous Na₂S₂O₄ / Erwaermen des Reaktionsgemisches mit Acetanhydrid 2: aqueous HCl; chlorine 3: pyridine 4: aq. NaOH solution

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]

31
[ 2127-09-5 ]
5-amino-pyridine-2-sulfonic acid-(5-iodo-[2]pyridylamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: aqueous Na₂S₂O₄ / Erwaermen des Reaktionsgemisches mit Acetanhydrid 2: aqueous HCl; chlorine 3: pyridine 4: aqueous NaOH

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]

32
[ 2127-09-5 ]
[ 855879-50-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: aqueous Na₂S₂O₄ / Erwaermen des Reaktionsgemisches mit Acetanhydrid 2: aqueous HCl; chlorine 3: acetone; aqueous NaOH

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]

33
[ 2127-09-5 ]
5-acetylamino-pyridine-2-sulfonic acid-[2]pyridylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: aqueous Na₂S₂O₄ / Erwaermen des Reaktionsgemisches mit Acetanhydrid 2: aqueous HCl; chlorine 3: pyridine

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]

34
[ 2127-09-5 ]
[ 861026-68-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: aqueous Na₂S₂O₄ / Erwaermen des Reaktionsgemisches mit Acetanhydrid 2: aqueous HCl; chlorine 3: pyridine

Reference： [1]Caldwell; Kornfeld [Journal of the American Chemical Society, 1942, vol. 64, p. 1695,1698]

35
[ 2127-09-5 ]
[ 6959-47-3 ]
5-nitro-2-[(2-pyridinylmethyl)sulfanyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In methanol at 20℃; for 0.25h;	161 Reference Example 161 5-nitro-2-pyridinethiol (6.0 g) was dissolved in an aqueous solution of methanol (150 ml), and to this solution was added sodium hydroxide (4.6 g) and then, 2-(chloromethyl)pyridine hydrochloride (7.6 g), and the mixture was stirred for 15 minutes at room temperature. The solvent was removed under reduced pressure, and water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 5-nitro-2-[(2-pyridinylmethyl)sulfanyl]pyridine (6.2 g). 1H-NMR (200 MHz, CDCl3) δ 4.65 (2H, s), 7.15 to 7.72 (1H, m), 7.35 (1H, d, J = 9.2 Hz), 7.43 to 7.48 (1H, m), 7.64 (1H, td, J = 7.6, 1.8 Hz), 8.23 (1H, d, J = 9.2, 3.0 Hz), 8.55 to 8.59 (1H, m), 9.23 to 9.25 (1H, m)

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1422228, 2004, A1 Location in patent: Page 209

36
[ 2127-09-5 ]
[ 6959-48-4 ]
5-nitro-2-[(3-pyridinylmethyl)sulfanyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In methanol; water for 0.5h;	163 Reference Example 163 5-nitro-2-pyridinethiol (5.0 g) was dissolved in an aqueous methanol solution (125 ml), and to this solution was added sodium hydroxide (3.84 g) and then, 3-(chloromethyl)pyridine hydrochloride (6.30 g), and the mixture was stirred for 30 minutes. The solvent was removed under reduced pressure, and the obtained residue was added to water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 5-nitro-2-[(3-pyridinylmethyl)sulfanyl]pyridine (6.0 g). 1H-NMR (200 MHz, CDCl3) δ 4.51 (2H, s), 7.21 to 7.32 (2H, m), 7.71 to 7.77 (1H, m), 8.24 (1H, dd, J = 8.8, 2.6 Hz), 8.68 (1H, d, J = 3.8 Hz), 9.27 (1H, d, J = 3.4 Hz)

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1422228, 2004, A1 Location in patent: Page 210

37
2-chloromethyl-3-(1-propyl)-3H-imidazole hydrochloride [ No CAS ]
[ 2127-09-5 ]
5-nitro-2-[[(1-propylimidazol-2-yl)methyl]sulfanyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 1h;	185 Reference Example 185 2-mercapto-5-nitropyridine (3.2 g) was dissolved in DMF (64 ml), potassium carbonate (8.5 g) and 2-chloromethyl-1-propylimidazole hydrochloride (4.8 g) were added to the mixture, and the mixture was stirred for 1 hour at room temperature. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 5-nitro-2-[[(1-propylimidazol-2-yl)methyl]sulfanyl]pyridine (4.8 g). 1H-NMR (200 MHz, CDCl3) δ 0.95 (3H, t, J = 7.4 Hz), 1.75 to 1.89 (2H, m), 3.96 (2H, t, J = 7.4 Hz), 4.66 (2H, s), 6.89 (1H, s), 6.99 (1H, s), 7.41 (1H, d, J = 8.8 Hz), 8.23 to 8.30 (1H, m), 9.25 to 9.27 (1H, m)

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1422228, 2004, A1 Location in patent: Page 214

38
3-(chloromethyl)-4-propyl-1H-1,2,4-triazole hydrochloride [ No CAS ]
[ 2127-09-5 ]
5-nitro-2-(4-propyl-4H-1,2,4-triazol-3-yl)methylthiopyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃;	43 Reference Example 43 2-mercapto-5-nitropyridine (5.0 g), 3-chloromethyl-4-propyl-4H-1,2,4-triazole hydrochloride (6.3 g) and potassium carbonate (11 g) was added to N,N-dimethylformamide (100 ml), and the mixture was stirred overnight at room temperature. The solvent was distilled off, and to the residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, to give 5-nitro-2-(4-propyl-4H-1,2,4-triazol-3-yl)methylthiopyridine (8.0 g) as brown crystals. 1H-NMR (dppm, CDCl3) 0.98 (3H, t, J = 7.3 Hz), 1.80 to 1.92 (2H, m), 4.00 (2H, t, J = 7.3 Hz), 4.75 (2H, s), 7.42 (1H, dd, J = 0.8, 9.0 Hz), 8.13 (1H, s), 8.31 (1H, dd, J =2.7, 9.0 Hz), 9.26 (1H, dd, J = 0.8, 2.7 Hz). IR (KBr) n: 2969, 1588, 1568, 1514, 1345 cm-1. Anal. calcd. for C11H13N5O2S: C, 47.30; H, 4.69; N, 25.07. Found C, 47.20; H, 4.63; N, 25.00.

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1422228, 2004, A1 Location in patent: Page 182

39
5-(chloromethyl)-1-propyl-1H-imidazole hydrochloride [ No CAS ]
[ 2127-09-5 ]
5-nitro-2-[[(1-propylimidazol-5-yl)methyl]sulfanyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 40h;	187 Reference Example 187 2-mercapto-5-nitropyridine (2.3 g) was dissolved in DMF (47 ml), potassium carbonate (6.2 g) and 5-chloromethyl-1-propylimidazole hydrochloride (3.5 g) was added to the mixture, and the mixture was stirred for 40 hours at room temperature. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 5-nitro-2-[[(1-propylimidazol-5-yl)methyl]sulfanyl]pyridine (2.9 g). 1H-NMR (200 MHz, CDCl3) δ 0.97 (3H, t, J = 7.2 Hz), 1.78 to 1.91 (2H, m), 3.88 to 3.96 (2H, m), 4.57 (2H, s), 7.05 (1H, s), 7.32 (1H, s), 8.23 to 8.30 (1H, s), 9.28 to 9.30 (1H, m)

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1422228, 2004, A1 Location in patent: Page 215

40
[ 2127-09-5 ]
[ 73291-09-5 ]
[ 866249-13-0 ]

Yield	Reaction Conditions	Operation in experiment
93.3%	With potassium carbonate; In acetone;	To 40 mg of 2-mercapto-5-nitropyridine was added 200 mL of acetone, and the solution was stirred while cooled with water. To this reaction solution were added 43.6 of <strong>[73291-09-5]4-chloromethylbenzaldehyde</strong> and 45 g of potassium carbonate, to conduct reaction. After the completion of the reaction, 1 L of water was added to the solution. The precipitated crystal was collected by filtration, washed with water, washed with methanol, and dried (yield amount 65.5 g, and yield 93.3%).

Reference： [1]Patent: WO2005/92847,2005,A1 .Location in patent: Page/Page column 32

41
[ 2127-09-5 ]
sodium carbonate monohydrate [ No CAS ]
[ 74-88-4 ]
[ 20885-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water	1.1 Step 1 Step 1 3-NITRO-6-(METHYLTHIO)PYRIDINE 2-Mercapto-5-nitro pyridine (20.0 g, 128 mmol) was suspended in water/ethanol (43 mL/13 mL). Sodium carbonate monohydrate (17.49 g, 141 mmol, dissolved in 86 mL of water) was added to the above slurry dropwise. Methyl iodide (20.0 g, 141 mmol) was added to the above mixture and the mixture was stirred at room temperature for one hour. The solid was filtered and washed with water and ethanol to provide the title compound in quantitative yield.

Reference： [1]Current Patent Assignee: PFIZER INC - US6531492, 2003, B1 Current Patent Assignee: PFIZER INC - US2002/58681, 2002, A1

42
[ 2127-09-5 ]
[ 540-51-2 ]
[ 886585-55-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetone at 55℃; for 1h;	2-[(5-Nitro-2-pyridinyl)thio]ethanol (7): A heterogeneous mixture of 2- mercapto-5-nitropyridine (4) (0.5Og, 3.2mmol), 2-bromoethanol (1) (0.238mL, 3.3mmol), and K2CO3 (2.Og, 14mmol) in acetone (1 ImL) was stirred at 55 °C for Ih. The cooled EPO reaction mixture was filtered through Celite, concentrated, and then purified by silica gel chromatography to give 2-[(5-nitro-2-pyridinyl)thio]ethanol (7) as an orange solid (0.545g, 2.72mmol). 1H NMR (CDCl3): δ 9.20 (d, J=3.0 Hz, IH), 8.23 (dd, J= 3.0 and 8.7 Hz, IH), 7.36 (d, J= 8.7 Hz, IH), 3.94 (t, J= 6.0 Hz, 2H), 3.46 (d, J= 6.0 Hz, 2H); LCMS: purity: 96%; MS (m/e): 201(MH+).

Reference： [1]Current Patent Assignee: RIGEL PHARMACEUTICALS INC - WO2006/50480, 2006, A2 Location in patent: Page/Page column 49; 50

43
[ 2127-09-5 ]
[ 27796-53-8 ]
[ 886585-53-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetone at 55℃; for 5h;	2-[(5-Nitro-2-pyridinyl)thio]ethyl-3-chlorobenzoate (5): A heterogeneous mixture of 2-mercapto-5-nitropyridine (4) (46mg, 0.29mmol), 2-bromoethyl-3- chlorobenzoate (3) (77mg, 0.29mmol), and K2CO3 (0.16Og, 1.1 mmol) in acetone (ImL) was stirred at 55 °C for 5h. The cooled reaction mixture was filtered through Celite, concentrated, and then purified by silica gel chromatography to give 2-[(5-nitro-2- pyridinyl)thio]ethyl-3-chlorobenzoate (5) as a white solid. IH NMR (CDC13): δ 9.22 (d, EPO J= 1.8 Hz, IH), 8.24 (dd, J= 2.4 and 9.0 Hz, IH), 7.95-7.91 (m, IH), 7.90 (t, J= 0.9 Hz, IH), 7.56-7.51 (m, IH), 7.39 (d, J= 8.1 Hz, IH), 7.34 (d, J= 8.1 Hz, IH), 4.61 (t, J= 6.6 Hz, 2H), 3.68 (t, J= 6.6 Hz, 2H)

Reference： [1]Current Patent Assignee: RIGEL PHARMACEUTICALS INC - WO2006/50480, 2006, A2 Location in patent: Page/Page column 48; 49

44
[ 2127-09-5 ]
[ 39684-80-5 ]
tert-butyl {2-[(5'-nitropyridin-2'-yl)sulfanyl]ethyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetone at 60℃; for 15h;	l-Amino-2-[(5-nitro-2-pyridinyl)thio]ethane (38): A heterogeneous solution of2-mercapto-5-nitropyridine (96mg, 0.62mmol), N-tert-butoxycarbonyl-amino-2- EPO bromoethane (0.14g, 0.63mmol), and K2CO3 (0.42g,, 3.0mmol) in acetone (1OmL) was heated at 60 °C for 15h. The cooled reaction mixture was filtered through Celite, concentrated, and then purified by silica gel chromatography to give N-tert- butoxycarbonyl-amino-2-(5-nitro-2-pyridinylthio)ethane (37), which was treated with trifluoroacetic acid (5 niL) in dichloromethane (5 mL) at room temperature for 30 min.The reaction mixture was concentrated and then residue was suspended in dichloromethane, washed with saturated NaHCO3 followed by brine, dried over anhydrous MgSO4 and concentrated to give l-amino-2-[(5-nitro-2-pyridinyl)thio]ethane (38) as a tan solid which was used without further purification. 1H NMR (DMSO-J6): δ 9.21 (d, J= 3.0 Hz, IH), 8.41 (dd, J= 2.4 and 8.7 Hz, IH), 7.81 (bs, 2H), 7.65 (d, J= 8.7Hz, IH), 3.44 (t, J= 6.6 Hz, 2H), 3.12 (t, J= 6.6 Hz, 2H).

Reference： [1]Current Patent Assignee: RIGEL PHARMACEUTICALS INC - WO2006/50480, 2006, A2 Location in patent: Page/Page column 54; 55

45
[ 2127-09-5 ]
[ 77-78-1 ]
[ 20885-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	In sodium hydroxide; water	1.t (at) (at) 4-Hydroxy-2-(6'-methylsulfinyl-3'-pyridylamino)-5-nitro-pyrimidine 4.68 gm (0.03 mol) of 2-mercapto-5-nitro-pyridine were dissolved, while gently heating, in a sodium hydroxide solution prepared by dissolving 1.32 gm (0.033 mol) of sodium hydroxide in 60 ml of water. 4.17 gm (0.033 mol) of dimethylsulfate were added to this solution, and the mixture was shaken well. The resulting precipitate was filtered off with suction, and the still moist product was recrystallized from ethanol. 2-Methylthio-5-nitro-pyridine was obtained. Yield: 4.5 gm (88.1%). M.p.: 111°-112° C.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US4415566, 1983, A

46
[ 2127-09-5 ]
2-propargylthio-5-nitropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetone	1 EXAMPLE 1 EXAMPLE 1 7 g of 5-nitro-pyridine-2-thiol are suspended in acetone, and 5 g of potassium carbonate are added. There are then added 6 g of 3-bromopropine-1, and, after the exothermic reaction has finished, the reaction mixture is refluxed for about 30 minutes. The solution obtained is poured onto ice, and the precipitate occurring is filtered off. The crude product is purified by recrystallisation from methanol to yield 2-propargylthio-5-nitropyridine, m.p. 98°-99.5° C.

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US4305946, 1981, A

47
[ 2127-09-5 ]
[ 941585-28-0 ]
[ 941585-48-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-mercapto-5-nitropyridine; 1′-N-(tert-butoxycarbonyl)-1′-demethyl-2,3,4-tris-O-(trimethylsilyl)lincomycin With triphenylphosphine; diethylazodicarboxylate In toluene at 0 - 20℃; for 16h; Stage #2: With hydrogenchloride; water In toluene	19.i Example 19: (i) 7-(5-Aminopyridin-2-ylthio)-1'-N-tert-butoxycarbonyl-1'-demeth yl-7-deoxy-7-epilincomycin The title compound (285 mg, yield 45%) was produced in the same manner as in step (ii) of Example 4, except that 667 mg (1.06 mmol) of 1'-N-tert-butoxycarbonyl-7-deoxy-7-epi-7-(5-nitropyridin-2-ylth io)lincomycin, which had been produced from the title compound in step (iii) of Example 15 and 2-mercapto-5-nitropyridine in the same manner as in step (ii) of Example 1 except that toluene was used instead of tetrahydrofuran, was used. 1H-NMR (300 MHz, CD3OD) δ: 1.49 (9H, s), 1.99 (3H, d, J = 20.1 Hz), 5.29 (1H, d, J = 5.1 Hz), 7.05 (1H, ddd, J = 2.7, 3.0, 8.1 Hz), 7.28 (1H, t, J = 8.1 Hz), 8.04 (1H, dd, J = 2.4, 9.3 Hz). MS (EI) m/z: 600 (M+).

Reference： [1]Current Patent Assignee: MEIJI HOLDINGS CO., LTD - EP1970377, 2008, A1 Location in patent: Page/Page column 58

48
[ 2127-09-5 ]
[ 941585-88-2 ]
[ 941585-90-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With triphenylphosphine; diethylazodicarboxylate In toluene at 0 - 20℃; for 7h;	43.i (i) Methyl 6-N-((2S,4R)-1-N-tert-butoxycarbonyl-4-butyl)pipecoloyl-7-deo xy-7-epi-7-(5-nitropyridin-2-ylthio)-1-thio-2,3,4-tri-o-trimethyls ilyl-α-lincosamide Triphenylphosphine (1.13 g, 4.10 mmol), 0.66 ml (4.07 mmol) of diethyl azodicarboxylate, and 651 mg (4.09 mmol) of 2-mercapto-5-nitropyridine were successively added under ice cooling to a solution of 2.00 g (2.71 mmol) of the title compound produced in step (i) of Example 42 in 40 ml of toluene, and the mixture was stirred at room temperature for 7 hr. The solvent was removed by distillation, and the residue was purified by column chromatography on silica gel (hexane : ethyl acetate = 8 : 1 to 6 : 1) to give 2.07 g (yield 87%) of the title compound. 1H-NMR (300 MHz, CDCl3) δ: 0.12 - 0.19 (27H, m), 1.48 (9H, s), 2.05 (3H, s), 4.55 (1H, dq, J = 3.3, 6.9 Hz), 5.14 (1H, d, J = 5.4 Hz), 7.24 (1H, d, J = 8.7 Hz), 8.20 (1H, dd, J = 2.7, 8.7 Hz), 9.21 (1H, dd, J = 0.3, 3.3 Hz). MS (FAB+) m/z: 875 (M+ + 1).

Reference： [1]Current Patent Assignee: MEIJI HOLDINGS CO., LTD - EP1970377, 2008, A1 Location in patent: Page/Page column 66

49
[ 2127-09-5 ]
[ 2110-78-3 ]
methyl 2-methyl-2-[(5-nitropyridin-2-yl)sulfanyl]propionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With ethyl-2-azidoacetate; phenyl diphenylphosphinite In toluene at 40℃; for 24h; Inert atmosphere;
97%	With ethyl-2-azidoacetate; phenyl diphenylphosphinite In toluene at 40℃; for 24h;

Reference： [1]Location in patent: experimental part Kuroda, Kiichi; Maruyama, Yuji; Hayashi, Yujiro; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 2009, vol. 82, # 3, p. 381 - 392]
[2]Location in patent: scheme or table Mukaiyama, Teruaki; Kuroda, Kiichi; Maruyama, Yuji [Heterocycles, 2010, vol. 80, # 1, p. 63 - 82]

50
[ 2127-09-5 ]
[ 352-11-4 ]
[ 878983-94-9 ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: 2-mercapto-5-nitropyridine With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: 1-chloromethyl-4-fluorobenzene In tetrahydrofuran at 20℃;	78 EXAMPLE 78: 2-(4-Fluoro-benzylsulfanyl)-5-nitro-pyridine; Sodium hydride (0.51 g, 0.0128 mol, 60% in mineral oil) was added portionwise to a suspension of 5-nitro- pyridine-2-thiol (2 g, 0.0128 mol) in 20 ml anhydrous tetrahydrofuran and the reaction mixture was stirred at room temperature for 60 minutes. 4-Fluorobenzyl chloride (1.85 g, 0.0128 mol) was then added to the reaction mixture and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated to dryness under reduced pressure, 70 ml water was added to the residue and the aqueous mixture was extracted with 100 ml ethyl acetate. The ethyl acetate extract was washed with 70 ml brine, dried (anhydrous sodium sulfate) and concentrated to dryness under reduced pressure. The crude product was purified by flash chromatography using silica gel to yield the title compound (1.01 g, 30% yield). 1H NMR (500 MHz, DMSO-D6): δ 4.52 (s, 2H), 7.2 (m, 2H), 7.5 (m, 2H), 7.6 (m, 1 H)1 8.4 (m, 1 H), 9.3 (s, 1 H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2007/91140, 2007, A1 Location in patent: Page/Page column 62

51
[ 2127-09-5 ]
[ 1309779-37-0 ]
[ 1309779-39-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	With triethylamine In dichloromethane at 0 - 20℃;

Reference： [1]Grayson, Elizabeth J.; Bernardes, Goncalo J. L.; Chalker, Justin M.; Boutureira, Omar; Koeppe, Julia R.; Davis, Benjamin G. [Angewandte Chemie - International Edition, 2011, vol. 50, # 18, p. 4127 - 4132]

52
[ 1309779-44-9 ]
[ 2127-09-5 ]
[ 1309779-46-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With tributylphosphine In 1,4-dioxane; chloroform; water Inert atmosphere;

Reference： [1]Grayson, Elizabeth J.; Bernardes, Goncalo J. L.; Chalker, Justin M.; Boutureira, Omar; Koeppe, Julia R.; Davis, Benjamin G. [Angewandte Chemie - International Edition, 2011, vol. 50, # 18, p. 4127 - 4132]

53
[ 2127-09-5 ]
[ 79130-51-1 ]
[ 1584114-13-5 ]

Yield	Reaction Conditions	Operation in experiment
46%	With triethylamine; sodium iodide In dichloromethane at 0 - 20℃;	10.ii Step (ii): N,N-Dimethyl-3-((5-nitropyridin-2-yl)thio)-3-phenylpropan-l-amine. Step (ii): N,N-Dimethyl-3-((5-nitropyridin-2-yl)thio)-3-phenylpropan-l-amine. To a cooled (0°C) solution of the product of the previous step (460 mg, 1.79 mmol, 1 eq.) in dichloromethane was added Et3N (0.4 ml, 2.68 mmol, 1.5 eq.), followed by Nal (135 mg, 0.9 mmol, 0.5 eq.) and 2-mercapto-5-nitropyridine (550 mg, 3,57 mmol, 2 eq.). The reaction mixture was stirred at rt overnight, washed with water, dried, filtered and concentrated. The crude compound (700 mg) was purified by reversed phase automated column chromatography (260 mg, 0.82 mmol, 46%).

Reference： [1]Current Patent Assignee: AAPA - WO2014/46544, 2014, A1 Location in patent: Page/Page column 21; 36

54
[ 2127-09-5 ]
[ 31716-01-5 ]
[ 1577171-76-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: 2-mercapto-5-nitropyridine With sodium hydroxide In methanol; water at 20℃; for 0.333333h; Inert atmosphere; Stage #2: pleuromutilin tosylate In methanol; dichloromethane; water at 20℃; Inert atmosphere;

Reference： [1]Ling, Chenyu; Fu, Liqiang; Gao, Suo; Chu, Wenjing; Wang, Hui; Huang, Yanqin; Chen, Xiaoyan; Yang, Yushe [Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4772 - 4795]

55
[ 2127-09-5 ]
[ 107-02-8 ]
[ 1415577-82-0 ]

Yield	Reaction Conditions	Operation in experiment
6.7 g	With triethylamine In tetrahydrofuran at 0℃; for 1.5h; Cooling with ice;	1-21 <Preparation of the Compound of the Formula 7-16> At RT, the compound of the formula (10-16) 5.0 g and tetrahydrofuran 30 ml were mixed and stirred, and the resulting mixtures were cooled to 0° C. and then thereto were added dropwise 95% acrolein 2.8 g and triethylamine 0.1 g. The resulting mixtures were stirred under ice-cooling for 1.5 hours. Thereafter, the resulting mixtures were added to water. The resulting mixtures were extracted with tert-butyl methyl ether. The organic layers were washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the compound of the formula (9-16) 6.7 g.
6.7 g	With triethylamine In tetrahydrofuran at 0℃; for 1.5h;	1-21 Production Example 1-21 Production of Compound Represented by Formula (1-73) Production of Compound Represented by Formula 7-16 5.0 g of the compound represented by Formula (10-16) and 30 ml of tetrahydrofuran were mixed at room temperature, followed by stirring, then, the obtained mixture was cooled to 0° C., and 2.8 g of 95% acrolein and 0.1 g of triethylamine were added dropwise thereto. The obtained mixture was stirred for 1.5 hours under ice-cooling. Next, water was added to the obtained mixture. The obtained mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure, whereby 6.7 g of the compound represented by Formula (9-16) was obtained.

Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US2014/228219, 2014, A1 Location in patent: Paragraph 0651-0655
[2]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US2015/289505, 2015, A1 Location in patent: Paragraph 0757-0758

56
[ 2127-09-5 ]
[ 33179-05-4 ]
(R)-2-((5-nitropyridin-2-yl)disulfanyl)propan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	Stage #1: 5-nitro-2-mercaptopyridine With sulfuryl dichloride In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: (2R)-2-mercaptopropan-1-ol In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;	2.a (a) (R)-2-((5-nitropyridin-2-yl)disulfanyl)propan-1-ol (10) (a) (R)-2-((5-nitropyridin-2-yl)disulfanyl)propan-1-ol (10) Sulfuryl chloride (2.35 mL of a 1.0M solution in DCM, 2.35 mmol) was added drop-wise to a stirred suspension of 5-nitropyridine-2-thiol 9 (334 mg, 2.14 mmol) in dry DCM (7.5 mL) at 0° C. (ice/acetone) under an argon atmosphere. The reaction mixture turned from a yellow suspension to a yellow solution and was allowed to warm to room temperature then stirred for 2 hours after which time the solvent was removed by evaporation in vacuo to provide a yellow solid. The solid was re-dissolved in DCM (15 mL) and treated drop-wise with a solution of (R)-2-mercaptopropan-1-ol (213 mg, 2.31 mmol) in dry DCM (7.5 mL) at 0° C. under an argon atmosphere. The reaction mixture was allowed to warm to room temperature and stirred for 20 hours at which point analysis by LC/MS revealed substantial product formation at retention time 1.41 minutes (ES+) m/z 247 ([M+H]+., 100% relative intensity). The precipitate was removed by filtration and the filtrate evaporated in vacuo to give an orange solid which was treated with H2O (20 mL) and basified with ammonium hydroxide solution. The mixture was extracted with DCM (3×25 mL) and the combined extracts washed with H2O (20 mL), brine (20 mL), dried (MgSO4), filtered and evaporated in vacuo to give the crude product. Purification by flash chromatography (gradient elution in 1% increments: 100% DCM to 98:2 v/v DCM/MeOH) gave the dilsulfide 10 as an oil (111 mg, 21% yield).
21%	Stage #1: 5-nitro-2-mercaptopyridine With sulfuryl dichloride In dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: (2R)-2-mercaptopropan-1-ol In dichloromethane at 0℃; for 20h; Inert atmosphere;	Sulfuryl chloride (2.35 mL of a 1.0M solution in DCM, 2.35 mmol) is added drop-wise to a stirred suspension of 5-nitropyridine-2-thiol (334 mg, 2.14 mmol) in dry DCM (7.5 mL) at 0° C. (ice/acetone) under an argon atmosphere. The reaction mixture turned from a yellow suspension to a yellow solution and is allowed to warm to room temperature then stirred for 2 hours after which time the solvent is removed by evaporation in vacuo to provide a yellow solid. The solid is re-dissolved in DCM (15 mL) and treated drop-wise with a solution of (R)-2-mercaptopropan-1-ol (213 mg, 2.31 mmol) in dry DCM (7.5 mL) at 0° C. under an argon atmosphere. The reaction mixture is allowed to warm to room temperature and stirred for 20 hours at which point analysis by LC/MS reveals substantial product formation at retention time 1.41 minutes (ES+) m/z 247 ([M+H]+, 100% relative intensity). The precipitate is removed by filtration and the filtrate evaporated in vacuo to give an orange solid which is treated with H2O (20 mL) and basified with ammonium hydroxide solution. The mixture is extracted with DCM (3×25 mL) and the combined extracts washed with H2O (20 mL), brine (20 mL), dried (MgSO4), filtered and evaporated in vacuo to give the crude product. Purification by flash chromatography (gradient elution in 1% increments: 100% DCM to 98:2 v/v DCM/MeOH) gives (R)-2-((5-nitropyridin-2-yl)disulfanyl)propan-1-olas an oil (111 mg, 21% yield).
21%	Stage #1: 5-nitro-2-mercaptopyridine With sulfuryl dichloride In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: (2R)-2-mercaptopropan-1-ol In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;	16 Example 16: Synthesis of Activated Linker A linker was activated with 5-nitropyridine-2-thiol as follows: Sulfuryl chloride (2.35 mL of a 1 .OM solution in DCM, 2.35 mmol) was added drop-wise to a stirred suspension of 5- nitropyridine-2-thiol (334 mg, 2.14 mmol) in dry DCM (7.5 mL) at 0°C (ice/acetone) under anargon atmosphere. The reaction mixture turned from a yellow suspension to a yellow solution and was allowed to warm to room temperature then stirred for 2 hours after which time the solvent was removed by evaporation in vacuo to provide a yellow solid. The solid was redissolved in DCM (15 mL) and treated drop-wise with a solution of (R)-2-mercaptopropan-1-ol (213 mg, 2.31 mmol) in dry DCM (7.5 mL) at 0°C under an argon atmosphere. The reactionmixture was allowed to warm to room temperature and stirred for 20 hours at which point analysis by LC/MS revealed substantial product formation at retention time 1.41 minutes (ES+) m/z 247 ([M+ Hib, 100% relative intensity). The precipitate was removed by filtration and the filtrate evaporated in vacuo to give an orange solid which was treated with H20 (20 mL) and basified with ammonium hydroxide solution. The mixture was extracted with DCM (3 x 25 mL)and the combined extracts washed with H20 (20 mL), brine (20 mL), dried (Mg504), filtered and evaporated in vacuo to give the cmde product. Purification by flash chromatography (gradient elution in 1% increments: 100% DCM to 98:2 v/v DCMIMeOH) gave (R)-2-((5- nitropyridin-2-yl)disulfanyl)propan-1-olas an oil (111 mg, 21% yield)

21%	Stage #1: 5-nitro-2-mercaptopyridine With sulfuryl dichloride In dichloromethane at 0 - 23℃; for 2h; Inert atmosphere; Stage #2: (2R)-2-mercaptopropan-1-ol In dichloromethane at 0 - 23℃; for 20h; Inert atmosphere;	Referring to Scheme 4, sulfuryl chloride (2.35 mL of a 1.OM solution in DCM, 2.35 mmol) was added drop-wise to a stirred suspension of 5-nitropyridine-2-thiol (334 mg, 2.14mmol) in dry DCM (7.5 mL) at 0°C (ice/acetone) under an argon atmosphere. The reaction mixture turned from a yellow suspension to a yellow solution and was allowed to warm to room temperature then stirred for 2 hours after which time the solvent was removed by evaporation in vacuo to provide a yellow solid. The solid was re-dissolved in DCM (15 mL) and treated drop-wise with a solution of(R)-2-mercaptopropan-1-ol (213 mg, 2.31 mmol) indry DCM (7.5 mL) at 0°C under an argon atmosphere. The reaction mixture was allowed to warm to room temperature and stirred for 20 hours at which point analysis by LC/MS revealed substantial product formation at retention time 1.41 minutes (ES+) m/z 247 ([M+ H], 1OO% relative intensity). The precipitate was removed by filtration and the filtrate evaporated in vacuo to give an orange solid which was treated with H20 (20 mL) and basifiedwith ammonium hydroxide solution. The mixture was extracted with DCM (3 x 25 mL) and the combined extracts washed with H20 (20 mL), brine (20 mL), dried (Mg504), filtered and evaporated in vacuo to give the crude product. Purification by flash chromatography (gradient elution in 1% increments: 100% DCM to 98:2 v/v DCM/MeOH) gave (R)-2-((5- nitropyridin-2-yl)disulfanyl)propan-1-ol 15 as an oil (111 mg, 21% yield).
21%	Stage #1: 5-nitro-2-mercaptopyridine With sulfuryl dichloride In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: (2R)-2-mercaptopropan-1-ol In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;	2 Example 2 Example 2 Sulfuryl chloride (2.35 mL of a 1.0M solution in DCM, 2.35 mmol) was added drop-wise to a stirred suspension of 5-nitropyridine-2-thiol (334 mg, 2.14 mmol) in dry DCM (7.5 mL) at 0° C. (ice/acetone) under an argon atmosphere. The reaction mixture turned from a yellow suspension to a yellow solution and was allowed to warm to room temperature then stirred for 2 hours after which time the solvent was removed by evaporation in vacuo to provide a yellow solid. The solid was re-dissolved in DCM (15 mL) and treated drop-wise with a solution of (R)-2-mercaptopropan-1-ol (213 mg, 2.31 mmol) in dry DCM (7.5 mL) at 0° C. under an argon atmosphere. The reaction mixture was allowed to warm to room temperature and stirred for 20 hours at which point analysis by LC/MS revealed substantial product formation at retention time 1.41 minutes (ES+) m/z 247 ([M+H]+., 100% relative intensity). The precipitate was removed by filtration and the filtrate evaporated in vacuo to give an orange solid which was treated with H2O (20 mL) and basified with ammonium hydroxide solution. The mixture was extracted with DCM (3×25 mL) and the combined extracts washed with H2O (20 mL), brine (20 mL), dried (MgSO4), filtered and evaporated in vacuo to give the crude product. Purification by flash chromatography (gradient elution in 1% increments: 100% DCM to 98:2 v/v DCM/MeOH) gave (R)-2-((5-nitropyridin-2-yl)disulfanyl)propan-1-ol as an oil (111 mg, 21% yield).
21%	Stage #1: 5-nitro-2-mercaptopyridine With sulfuryl dichloride In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: (2R)-2-mercaptopropan-1-ol In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;	Scheme 4 Referring to Scheme 4, sulfuryl chloride (2.35 mL of a 1.0M solution in DCM, 2.35 mmol) was added drop-wise to a stirred suspension of 5-nitropyridine-2-thiol (334 mg, 2.14 mmol) in dry DCM (7.5 mL) at 0°C (ice/acetone) under an argon atmosphere. The reaction mixture turned from a yellow suspension to a yellow solution and was allowed to warm to room temperature then stirred for 2 hours after which time the solvent was removed by evaporation in vacuo to provide a yellow solid. The solid was re-dissolved in DCM (15 mL) and treated drop-wise with a solution of (R)-2-mercaptopropan-1-ol (213 mg, 2.31 mmol) in dry DCM (7.5 mL) at 0°C under an argon atmosphere. The reaction mixture was allowed to warm to room temperature and stirred for 20 hours at which point analysis by LC/MS revealed substantial product formation at retention time 1.41 minutes (ES+) m/z 247 ([M+ H]+., ~100% relative intensity). The precipitate was removed by filtration and the filtrate evaporated in vacuo to give an orange solid which was treated with H2O (20 mL) and basified with ammonium hydroxide solution. The mixture was extracted with DCM (3 x 25 mL) and the combined extracts washed with H2O (20 mL), brine (20 mL), dried (MgSO4), filtered and evaporated in vacuo to give the crude product. Purification by flash chromatography (gradient elution in 1% increments: 100% DCM to 98:2 v/v DCM/MeOH) gave (R)-2-((5- nitropyridin-2-yl)disulfanyl)propan-1-ol 15 as an oil (111 mg, 21% yield).
21%	Stage #1: 5-nitro-2-mercaptopyridine With sulfuryl dichloride In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: (2R)-2-mercaptopropan-1-ol In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;	Scheme 4 Referring to Scheme 4, sulfuryl chloride (2.35 mL of a 1.0M solution in DCM, 2.35 mmol) was added drop-wise to a stirred suspension of 5-nitropyridine-2-thiol (334 mg, 2.14 mmol) in dry DCM (7.5 mL) at 0°C (ice/acetone) under an argon atmosphere. The reaction mixture turned from a yellow suspension to a yellow solution and was allowed to warm to room temperature then stirred for 2 hours after which time the solvent was removed by evaporation in vacuo to provide a yellow solid. The solid was re-dissolved in DCM (15 mL) and treated drop-wise with a solution of (R)-2-mercaptopropan-1-ol (213 mg, 2.31 mmol) in dry DCM (7.5 mL) at 0°C under an argon atmosphere. The reaction mixture was allowed to warm to room temperature and stirred for 20 hours at which point analysis by LC/MS revealed substantial product formation at retention time 1.41 minutes (ES+) m/z 247 ([M+ H]+., ~100% relative intensity). The precipitate was removed by filtration and the filtrate evaporated in vacuo to give an orange solid which was treated with H2O (20 mL) and basified with ammonium hydroxide solution. The mixture was extracted with DCM (3 x 25 mL) and the combined extracts washed with H2O (20 mL), brine (20 mL), dried (MgSO4), filtered and evaporated in vacuo to give the crude product. Purification by flash chromatography (gradient elution in 1% increments: 100% DCM to 98:2 v/v DCM/MeOH) gave (R)-2-((5- nitropyridin-2-yl)disulfanyl)propan-1-ol 15 as an oil (111 mg, 21% yield).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2016/74527, 2016, A1 Location in patent: Paragraph 0506; 0507
[2]Current Patent Assignee: ROCHE HOLDING AG - US2016/159910, 2016, A1 Location in patent: Page/Page column 84
[3]Current Patent Assignee: ROCHE HOLDING AG - WO2017/64675, 2017, A1 Location in patent: Page/Page column 117
[4]Current Patent Assignee: ROCHE HOLDING AG - WO2017/201449, 2017, A1 Location in patent: Page/Page column 155
[5]Current Patent Assignee: ROCHE HOLDING AG - US2016/75787, 2016, A1 Location in patent: Paragraph 0571
[6]Current Patent Assignee: ROCHE HOLDING AG - WO2022/20288, 2022, A1 Location in patent: Page/Page column 122
[7]Current Patent Assignee: ROCHE HOLDING AG - WO2022/20288, 2022, A1 Location in patent: Page/Page column 122

57
[ 2127-09-5 ]
tert-butyl (2-((S)-2-(hydroxymethyl)-4-methylenepyrrolidine-1-carbonyl)-5-((5-(4-((S)-2-(hydroxymethyl)-4-methylenepyrrolidine-1-carbonyl)-2-methoxy-5-((((R)-2-((5-nitropyridin-2-yl)disulfanyl)propoxy)carbonyl)amino)phenoxy)pentyl)oxy)-4-methoxyphenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 - 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.75 h / Inert atmosphere 3.1: pyridine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere 4.1: acetic acid; water / tetrahydrofuran / 16 h
	Multi-step reaction with 4 steps 1.1: sulfuryl dichloride / dichloromethane / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.75 h / Inert atmosphere 3.1: pyridine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere 4.1: acetic acid / tetrahydrofuran; water / 16 h
	Multi-step reaction with 4 steps 1.1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 - 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.5 h / 20 °C 3.1: pyridine / dichloromethane / 3 h / 20 °C 4.1: acetic acid / tetrahydrofuran; water / 24 h / 20 °C

Multi-step reaction with 5 steps 1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 0.5 h / 20 °C 4: pyridine / dichloromethane / 3 h / 20 °C 5: acetic acid / water; tetrahydrofuran / 24 h / 20 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2016/74527, 2016, A1
[2]Current Patent Assignee: ROCHE HOLDING AG - US2016/159910, 2016, A1
[3]Current Patent Assignee: ROCHE HOLDING AG - WO2017/64675, 2017, A1
[4]Current Patent Assignee: ROCHE HOLDING AG - US2017/95570, 2017, A1

58
[ 2127-09-5 ]
tert-butyl (11S,11aS)-11-hydroxy-8-((5-(((11S,11aS)-11-hydroxy-7-methoxy-2-methylene-10-(((R)-2-((5-nitropyridin-2-yl)disulfanyl)propoxy)carbonyl)-5-oxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yl)oxy)pentyl)oxy)-7-methoxy-2-methylene-5-oxo-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10(5H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 - 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.75 h / Inert atmosphere 3.1: pyridine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere 4.1: acetic acid; water / tetrahydrofuran / 16 h 5.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -45 °C / Inert atmosphere 5.2: 1.5 h / 20 °C / Inert atmosphere
	Multi-step reaction with 5 steps 1.1: sulfuryl dichloride / dichloromethane / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.75 h / Inert atmosphere 3.1: pyridine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere 4.1: acetic acid / tetrahydrofuran; water / 16 h 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -45 °C / Inert atmosphere 5.2: 1.5 h / -45 - 20 °C / Inert atmosphere
	Multi-step reaction with 5 steps 1.1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 - 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.5 h / 20 °C 3.1: pyridine / dichloromethane / 3 h / 20 °C 4.1: acetic acid / tetrahydrofuran; water / 24 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C

Multi-step reaction with 6 steps 1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 0.5 h / 20 °C 4: pyridine / dichloromethane / 3 h / 20 °C 5: acetic acid / water; tetrahydrofuran / 24 h / 20 °C 6: Dess-Martin periodane / dichloromethane / 2 h / 25 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2016/74527, 2016, A1
[2]Current Patent Assignee: ROCHE HOLDING AG - US2016/159910, 2016, A1
[3]Current Patent Assignee: ROCHE HOLDING AG - WO2017/64675, 2017, A1
[4]Current Patent Assignee: ROCHE HOLDING AG - US2017/95570, 2017, A1

59
[ 2127-09-5 ]
(11S,11aS)-I-2-((5-nitropyridin-2-yl)disulfanyl)propyl 11-hydroxy-7-methoxy-8-((5-(((S)-7-methoxy-2-methylene-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a] [1,4]diazepin-8-yl)oxy)pentyl)oxy)-2-methylene-5-oxo-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolol[1 ,2-a][1 ,4]diazepine-10(5H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 - 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.75 h / Inert atmosphere 3.1: pyridine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere 4.1: acetic acid; water / tetrahydrofuran / 16 h 5.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -45 °C / Inert atmosphere 5.2: 1.5 h / 20 °C / Inert atmosphere 6.1: water; trifluoroacetic acid / 0.5 h / 0 °C
	Multi-step reaction with 6 steps 1.1: sulfuryl dichloride / dichloromethane / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.75 h / Inert atmosphere 3.1: pyridine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere 4.1: acetic acid / tetrahydrofuran; water / 16 h 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -45 °C / Inert atmosphere 5.2: 1.5 h / -45 - 20 °C / Inert atmosphere 6.1: trifluoroacetic acid / water / 0.5 h / 0 °C
	Multi-step reaction with 6 steps 1.1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 - 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.5 h / 20 °C 3.1: pyridine / dichloromethane / 3 h / 20 °C 4.1: acetic acid / tetrahydrofuran; water / 24 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C 6.1: tetrahydrofuran; water / 0.5 h / 0 °C / Acidic conditions

Multi-step reaction with 7 steps 1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 0.5 h / 20 °C 4: pyridine / dichloromethane / 3 h / 20 °C 5: acetic acid / water; tetrahydrofuran / 24 h / 20 °C 6: Dess-Martin periodane / dichloromethane / 2 h / 25 °C 7: trifluoroacetic acid / 0.33 h / 0 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2016/74527, 2016, A1
[2]Current Patent Assignee: ROCHE HOLDING AG - US2016/159910, 2016, A1
[3]Current Patent Assignee: ROCHE HOLDING AG - WO2017/64675, 2017, A1
[4]Current Patent Assignee: ROCHE HOLDING AG - US2017/95570, 2017, A1

60
[ 2127-09-5 ]
(R)-2-((5-nitropyridin-2-yl)disulfanyl)propyl carbonochloridate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 - 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.75 h / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: sulfuryl dichloride / dichloromethane / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.75 h / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 - 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.5 h / 20 °C

	Multi-step reaction with 2 steps 1.1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 23 °C / Inert atmosphere 1.2: 20 h / 0 - 23 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.5 h / 23 °C
	Multi-step reaction with 3 steps 1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 0.5 h / 20 °C
	Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 0 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 - 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 20 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2016/74527, 2016, A1
[2]Current Patent Assignee: ROCHE HOLDING AG - US2016/159910, 2016, A1
[3]Current Patent Assignee: ROCHE HOLDING AG - WO2017/64675, 2017, A1
[4]Current Patent Assignee: ROCHE HOLDING AG - WO2017/201449, 2017, A1
[5]Current Patent Assignee: ROCHE HOLDING AG - US2017/95570, 2017, A1
[6]He, Lei; Wang, Liangliang; Wang, Zhisong; Li, Tiantian; Chen, Hui; Zhang, Yaning; Hu, Zeping; Dimitrov, Dimiter S.; Du, Juanjuan; Liao, Xuebin [Journal of Medicinal Chemistry, 2021, vol. 64, # 21, p. 15716 - 15726]
[7]Current Patent Assignee: ROCHE HOLDING AG - WO2022/20288, 2022, A1

61
[ 2127-09-5 ]
tert-butyl (2-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-methylenepyrrolidine-1-carbonyl)-5-((5-(4-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-methylenepyrrolidine-1-carbonyl)-2-methoxy-5-((((R)-2-((5-nitropyridin-2-yl)disulfanyl)propoxy)carbonyl)amino)phenoxy)pentyl)oxy)-4-methoxyphenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 - 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.75 h / Inert atmosphere 3.1: pyridine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: sulfuryl dichloride / dichloromethane / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.75 h / Inert atmosphere 3.1: pyridine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 0 - 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0.5 h / 20 °C 3.1: pyridine / dichloromethane / 3 h / 20 °C

Multi-step reaction with 4 steps 1: sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 0.5 h / 20 °C 4: pyridine / dichloromethane / 3 h / 20 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2016/74527, 2016, A1
[2]Current Patent Assignee: ROCHE HOLDING AG - US2016/159910, 2016, A1
[3]Current Patent Assignee: ROCHE HOLDING AG - WO2017/64675, 2017, A1
[4]Current Patent Assignee: ROCHE HOLDING AG - US2017/95570, 2017, A1

62
[ 2127-09-5 ]
2-(2-pyridyldisulfanyl)propyl N-methyl-N-[2-[methyl-[2-oxo-2-[2,5,12-trihydroxy-7-methoxy-4-[(9-methoxy-1-methyl-3,4,4a,6,7,9,9a,10a-octahydro-1H-pyrano[1,2]oxazolo[3,4-b][1,4]oxazin-3-yl)oxy]-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]ethoxy]carbonylamino]ethyl]carbamate [ No CAS ]
[2-oxo-2-[2,5,12-trihydroxy-7-methoxy-4-[(9-methoxy-1-methyl-3,4,4a,6,7,9,9a,10a-octahydro-1H-pyrano[1,2]oxazolo[3,4-b][1,4]oxazin-3-yl)oxy]-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]ethyl]-N-methyl-N-[2-[methyl-[2-[(5-nitro-2-pyridyl)disulfanyl]propoxycarbonyl]amino]ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.94%	In N,N-dimethyl-formamide at 20℃; for 2h;	1 Synthesis of [2-oxo-2-[2,5,12-trihydroxy-7-methoxy-4-[(9-methoxy-1-methyl-3,4,4a,6,7,9,9a,10a-octahydro-1H-pyrano[1,2]oxazolo[3,4-b][1,4]oxazin-3-yl)oxy]-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]ethyl]N-methyl-N-[2-[methyl-[2-[(5-nitro-2-pyridyl)disulfanyl]propoxycarbonyl]amino]ethyl]carbamate General procedure: To a solution of 2-(2-pyridyldisulfanyl)propyl N-methyl-N-[2-[methyl-[2-oxo-2-[2,5,12-trihydroxy-7-methoxy-4-[(9-methoxy-1-methyl-3,4,4a,6,7,9,9a,10a-octahydro-1H-pyrano[1,2]oxazolo[3,4-b][1,4]oxazin-3-yl)oxy]-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]ethoxy]carbonyl-amino]ethyl]carbamate LD-56 (10 mg, 10.17 umol) in DMF (1 mL) was added a solution of 5-nitropyridine-2-thiol 60a (15.89 mg, 101.72 umol) at 20° C. The reaction mixture was stirred at 20° C. for 2 h. The reaction mixture was diluted with DCM (10 mL) and then washed with water (5 mL), aq.NaHCO3 (5 mL) and brine (5 mL). The organic layer was dried and concentrated. The residue was purified by prep-TLC (DCM:MeOH=25:1) to give pure LD-60 (7 mg, 66.94%) as a red solid. LCMS: (10-80, CD, 7.0 min), 3.782 min, Ms=1028.2 (M+1); 1H NMR (400 MHz, CDCl3) δ 13.83 (s, 1H), 13.19 (s, 1H), 9.18 (s, 1H), 8.31 (d, 1H, J=7.6 Hz), 7.97 (d, 1H, J=8.0 Hz), 7.86 (d, 1H, J=8.4 Hz), 7.73 (t, 1H, J=8.4 Hz), 7.33 (d, 1H, J=8.4 Hz), 5.41 (s, 1H), 5.29-5.05 (m, 3H), 4.89-4.75 (m, 1H), 4.64 (s, 1H), 4.40 (s, 1H), 4.13 (s, 2H), 4.09-3.80 (m, 6H), 3.58-3.12 (m, 12H), 3.05-2.85 (m, 7H), 2.78-2.42 (m, 3H), 2.12-1.85 (m, 2H), 1.72-1.55 (m, 1H), 1.38-1.25 (m, 6H)

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2016/74528, 2016, A1 Location in patent: Paragraph 0331-0333

63
[ 2127-09-5 ]
2-(2-pyridyl-disulfanyl)propyl 3-[6-[1-(chloromethyl)-5-phosphonooxy-1,2-dihydrobenzo[e]indol-3-yl]-6-oxo-hexoxy]-6-hydroxy-2-methoxy-11-oxo-6a,7,8,9-tetrahydro-6H-pyrrolo[2,1-c][1,4]benzo-diazepine-5-carboxylate [ No CAS ]
2-((5-nitropyridin-2-yl)disulfanyl)propyl(11aS)-8-((6-((S)-1-(chloromethyl)-5-(phosphonooxy)-1,2-dihydro-3H-benzo[e]indol-3-yl)-6-oxohexyl)oxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10(5H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47.62%	In N,N-dimethyl-formamide at 20℃; for 1h;	2.B B. Synthesis of CBI-PBD linker drug Intermediates Compound 85 was prepared as follows: To a solution of 82 (15 mg, 16.64umol) in DMF (1.0 mL) was added a solution of 5-nitropyridine-2-thiol (25.99 mg, 166.41 umol) at 20° C. The reaction mixture was stirred at 20° C. for 1 h. The reaction mixture was filtered and purified by prep-HPLC (FA) to give 2-((5-nitropyridin-2-yl)disulfanyl)propyl (llaS)-8-((6-((S)-l-(chloromethyl)-5-(phosphonooxy)-l,2-dihydro-3H-benzo[e]indol-3-yl)-6-oxohexyl)oxy)-l 1 -hydroxy-7 -methoxy-5-oxo-2,3,11,11a-tetrahydro-1 H-benzo [e]pyrrolo [ 1,2-a] [ 1,4]diazepine-10 (5H)-carboxylate 85(7.5 mg, 47.62%) as a gray solid. LCMS: (10-80, CD_NEG, 3.0 min), 1.161 min,MS=944.2 [M-l]-; XHNMR (400 MHz, CDC13) 8 9.18 (s, 1H),8.41 (br, 1H, J=7.6 Hz), 8.11 (br, 1H), 7.80 (d, 1H, J=8.0 Hz), 7.67 (d, 1H,J=8.4 Hz), 7.46 (d, 1H, J=7.6 Hz), 7.30 (s, 1H), 7.07 (s, 1H), 6.99-6.93 (m,1H), 5.52 (d, 1H, J=8.4 Hz), 4.26-4.14 (m, 4H), 3.98-3.80 (m, 4H), 3.76 (s,3H), 3.40-3.26 (m, 5H), 2.40-2.28 (m, 2H), 2.10-1.80 (m, 5H), 1.79-1.55 (m,5H), 1.40 (br, 1H), 1.19 (s, 1H), 1.12 (d, 3H, J=8.8 Hz).

Reference： [1]Current Patent Assignee: GENE THAKE; ROCHE HOLDING AG; PRYSMIAN SPA; UNITY ALUMINUM - US2016/96893, 2016, A1 Location in patent: Paragraph 0653-0654

64
[ 2127-09-5 ]
pleuromutilin-22-O-p-toluenesulfonate [ No CAS ]
14-O-[(5-nitropyridine)-2-thioacetyl]mutilin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: 2-mercapto-5-nitropyridine With sodium ethanolate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: pleuromutilin-22-O-p-toluenesulfonate In N,N-dimethyl-formamide at 20℃; for 4h;	7.b 14-O-[(5-nitropyridine)-2-thioacetyl]mutilin 2-mercapto-5-nitropyridine (200 mg, 1.3 mmol) was dissolved in DMF (8 mL), sodium ethoxide (109 mg, 1.6 mmol) was added, Ar gas was protected at room temperature for 30 min.A solution of Pleuromutilin-22-O-p-toluenesulfonate in DMF (68 lmg, 1.3 mmol) was injected and reacted at room temperature for 4 h. The solvent was removed by evaporation and the residue was chromatographed on silica gel to give compound 7 as a pale yellow solid (300 mg, 45%).

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Shanghai Institute of Materia Medica (in: CAS); SHIONOGI & CO., LTD. - CN103626693, 2016, B Location in patent: Paragraph 0178-0180

65
[ 2127-09-5 ]
C₅H₃ClN₂O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuryl dichloride In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	2 Synthesis of (11S,11aS)-(R)-2-((5-nitropyridin-2-yl)disulfanyl)propyl 11-hydroxy-7-methoxy-8-((5-(((S)-7-methoxy-2-methylene-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yl)oxy)pentyl)oxy)-2-methylene-5-oxo-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10(5H)-carboxylate (LD-51) Sulfuryl chloride (2.35 mL of a 1.0M solution in DCM, 2.35 mmol) was added drop-wise to a stirred suspension of 5-nitropyridine-2-thiol (334 mg, 2.14 mmol) in dry DCM (7.5 mL) at 0° C. (ice/acetone) under an argon atmosphere. The reaction mixture turned from a yellow suspension to a yellow solution and was allowed to warm to room temperature then stirred for 2 hours after which time the solvent was removed by evaporation in vacuo to provide a yellow solid. The solid was re-dissolved in DCM (15 mL) and treated drop-wise with a solution of (R)-2-mercaptopropan-1-ol (213 mg, 2.31 mmol) in dry DCM (7.5 mL) at 0° C. under an argon atmosphere. The reaction mixture was allowed to warm to room temperature and stirred for 20 hours at which point analysis by LC/MS revealed substantial product formation at retention time 1.41 minutes (ES+) m/z 247 ([M+H]+, ˜100% relative intensity). The precipitate was removed by filtration and the filtrate evaporated in vacuo to give an orange solid which was treated with H2O (20 mL) and basified with ammonium hydroxide solution. The mixture was extracted with DCM (3*25 mL) and the combined extracts washed with H2O (20 mL), brine (20 mL), dried (MgSO4), filtered and evaporated in vacuo to give the crude product. Purification by flash chromatography (gradient elution in 1% increments: 100% DCM to 98:2 v/v DCM/MeOH) gave (R)-2-((5-nitropyridin-2-yl)disulfanyl)propan-1-ol 15 as an oil (111 mg, 21% yield).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2017/95570, 2017, A1 Location in patent: Paragraph 0598; 0599

66
[ 2127-09-5 ]
1,2,3,4-tetra-O-acetyl-β-L-fucopyranose [ No CAS ]
C₁₇H₂₀N₂O₉S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With ytterbium(III) nitrate at 40℃; for 5h; Inert atmosphere; Ionic liquid; Sealed tube; Microwave irradiation;	11 Example 11: Preparation of 2,3,4-triacetyl-1- (5-nitro-2-pyridyl) mercapto-alpha-L-fucopyranoside Weigh 0.391 g Yb (NO3) 3 respectively, 0.33 g of tetraacetylated fucose, 0.155 g of 5-nitro-2-mercaptopyridine, In parallel reaction tube. The ionic liquid PFIL-4 [R1 = propyl, R2 = hydrogen, R3, R4 = ethoxy, n = 5, X = PF6] 3 mL, Closed reaction tube, Stirring reaction, Microwave irradiation using intermittent, Power 500W, Each irradiation for 5 minutes, Stop irradiation for 1 minute. Reaction for 5 hours, Temperature control at 40 degrees Celsius. The reaction was terminated by adding water. After silica gel column separation,0.31 g of glycoside 1-2 was obtained, Yield 73%. Ionic liquids can be reused, Yield no significant change.

Reference： [1]Current Patent Assignee: NINGBO UNIVERSITY - CN106478749, 2017, A Location in patent: Paragraph 0055; 0056; 0057; 0058; 0059; 0060; 0061-0066

67
[ 456-24-6 ]
[ 2127-09-5 ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 12738 - 12741

68
[ 2127-09-5 ]
[(1R,4R,6R,9R,10S)-4,12,12-trimethyl-5-oxatricyclo[8.2.0.0^4,6]dodecan-9-yl]methanethiol [ No CAS ]
5-nitro-2-([(1R,4R,6R,9R,10S)-4,12,12-trimethyl-5-oxatricyclo[8.2.0.0^4,6]dodecan-9-yl]methyl}disulfanyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	Stage #1: 2-mercapto-5-nitropyridine With 1,2,3-Benzotriazole; N-chlorobenzotriazole In dichloromethane at -78 - -50℃; for 2h; Inert atmosphere; Stage #2: [(1R,4R,6R,9R,10S)-4,12,12-trimethyl-5-oxatricyclo[8.2.0.0^4,6]dodecan-9-yl]methanethiol In dichloromethane at -50 - 0℃; Inert atmosphere;

Reference： [1]Gyrdymova, Yulia V.; Sudarikov, Denis V.; Shevchenko, Oksana G.; Rubtsova, Svetlana A.; Slepukhin, Pavel A.; Kutchin, Aleksandr V. [Chemistry and biodiversity, 2017, vol. 14, # 12]

69
[ 2127-09-5 ]
[ 170850-45-0 ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 15916 - 15923

70
[ 2127-09-5 ]
2,3,5-tris-O-(tert-butyldimethysilyl)ribofuranosyl iodide [ No CAS ]
5-nitro-2-pyridinyl 2,3,5-tris-O-(tert-butyldimethylsilyl)-1-thio-α-D-ribofuranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.0284 g	With N,N-diethylaniline In dichloromethane at -20℃; for 4h; Inert atmosphere; Molecular sieve; stereoselective reaction;

Reference： [1]Oka, Natsuhisa; Mori, Ayumi; Ando, Kaori [European Journal of Organic Chemistry, 2018, vol. 2018, # 45, p. 6355 - 6362]

71
[ 2127-09-5 ]
[ 73303-88-5 ]
2-methyl-2-[(5-nitro-2-pyridinyl)disulfanyl]propan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 2-mercapto-5-nitropyridine With sulfuryl dichloride In dichloromethane at 4 - 20℃; for 2h; Inert atmosphere; Stage #2: 2-methyl-1-hydroxypropane-2-thiol In dichloromethane at 4 - 20℃; for 20h; Inert atmosphere;	Intermediate 1-3: 2-methyl-2-[(5-nitro-2-pyridyl)disulfanyl]propan-l-ol SO2CI2 (0.382 mL, 4.71 mmol) was added drop-wise to a stirred suspension of 5- nitropyridine-2-thiol (668 mg, 4.28 mmol) in dry DCM (15 mL) at 4° C under an N2 atmosphere. The reaction mixture turned from a yellow suspension to a yellow solution and was allowed to warm to room temperature with stirring for 2 hours, after which time the mixture was concentrated to provide a yellow solid. The solid was re-dissolved in DCM (15 mL) and treated drop-wise with a solution of 2-methyl-2-sulfanyl-propan-l-ol (454 mg, 4.28 mmol) in dry DCM (10 mL) at 4° C under an N2 atmosphere. The reaction mixture was allowed to warm to room temperature and stirred for 20 hours. The reaction was monitored by LC/MS for the desired product mass. To the mixture was added 50 mL of H2O and the diluted mixture was treated with ammonium hydroxide solution. The reaction mixture was diluted with 50 mL of EtO Ac, partitioned, and separated. The organic phase was dried with MgS04, filtered, and concentrated to give the crude product. The crude mixture was purified (S1O2, 0-50% EtO Ac/hexanes) to give 721 mg, 65% yield of 2-methyl-2-[(5-nitro-2- pyridyl)disulfanyl]propan-l-ol. MS m/z found 261.7 [M+H]+.

Reference： [1]Current Patent Assignee: CYBREXA 1 - WO2019/136298, 2019, A1 Location in patent: Page/Page column 91; 92

72
[ 53939-30-3 ]
[ 2127-09-5 ]
C₁₀H₆BrN₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.3%	With potassium carbonate In dimethyl sulfoxide at 90℃; for 12h;	3 <Preparation Example 3> Preparation of a compound of Formula 1-3 After dissolving the compound of formula L (20.0 g, 128.2 mmol) and formula H (24.5, 128.2 mmol) in DMSO (200 mL), potassium carbonate (26.5 g, 192.3 mmol) was added and stirred at 90°C. After 12 hours, water (200 ml) was added and the solid obtained by filtration was washed with water and ethanol to prepare a compound of Formula M (32.0 g, yield 80.3%).

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2020/59960, 2020, A Location in patent: Paragraph 0220-0223

73
[ 623-73-4 ]
[ 2127-09-5 ]
ethyl 2-(5-nitropyridine-2-sulfanyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In water; acetonitrile at 20℃; for 6h; Irradiation;	19 A preparation method of sulfide This method refers to adding 0.3 mmol of 5-nitropyridine-2-thiol and 0.6 mmol (2 equiv) of ethyl diazoacetate in a mixed solvent of acetonitrile and water, and irradiating at room temperature with 23 W compact fluorescent lamp (CFL) The reaction was stirred for 6 h (the completion of the reaction was monitored by TLC) to obtain a mixture. The mixture was quenched with saturated brine (2 mL) and extracted with ethyl acetate (3×5 mL) to obtain an organic phase. The organic phase was dried over anhydrous Na2SO4, filtered and distilled under reduced pressure to remove the solvent, and finally passed through a silica gel column. After analysis, 2-(5-nitropyridine-2-thio) ethyl acetate 3sa is obtained.
87%	In water; acetonitrile at 20℃; for 6h; Irradiation;

Reference： [1]Current Patent Assignee: GANSU AGRICULTURAL UNIVERSITY - CN111808003, 2020, A Location in patent: Paragraph 0018; 0036-0037
[2]Chen, Shuwen; Huo, Congde; Liu, Cai; Ma, Ben; Song, Menghui; Wang, Ganggang; Yang, Jingya; Zhou, Hongyan [Organic and Biomolecular Chemistry, 2020, vol. 18, # 46, p. 9494 - 9498]

74
[ 2127-09-5 ]
C₁₁H₁₄ClN₃O₂ [ No CAS ]
1-[4-(5-hydroxypyridin-2-yl)piperazin-1-yl]-2-(5-nitropyridin-2-ylsulfanyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	In ethanol at 95℃; for 15h;	19.II 0559) Step-II: A solution of compound 19A (0.38 g, 1.0 eq) in ethanol (25 ml) was added to 5-nitropyridine-2-thiol (0.232 g, 1.0 eq) at room temperature and the resultant reaction mixture was heated to 95°C for 15 hours. On completion of reaction, the reaction mixture was cooled to 0-5°C. Precipitated solid was filtered and washed with diethyl ether (2 x 10 ml). The solid obtained was dried under reduced pressure at 55°C for 3 hours to afford pure compound (1.97) (0.35 g, yield: 66%) as a red brown colored solid.

Reference： [1]Current Patent Assignee: SUN PHARMA ADVANCED RESEARCH COMPANY LIMITED - WO2021/74898, 2021, A1 Location in patent: Page/Page column 112

75
[ 2127-09-5 ]
benzyl (6R,11R)-6-((2-(benzyloxy)-2-oxoethyl)carbamoyl)-11-((tertbutoxycarbonyl)amino)-2,2-dimethyl-4,12-dioxo-3-oxa-8,9-diselena-5,13-diazapentadecan-15-oate [ No CAS ]
benzyl (R)-(2-((tert-butoxycarbonyl)amino)-3-(((5-nitropyridin-2-yl)thio)selanyl)propanoyl)glycinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With rose bengal In acetonitrile for 1h; Irradiation;

Reference： [1]Arsenyan, Pavel; Dimitrijevs, Pavels; Lapcinska, Sindija [Advanced Synthesis and Catalysis, 2021, vol. 363, # 16, p. 3968 - 3972]

76
[ 2127-09-5 ]
(x)C₂HF₃O₂*C₅₂H₇₆N₆O₁₆Se₂ [ No CAS ]
tert-butyl N₅-((R)-1-((2-(benzyloxy)-2-oxoethyl)amino)-3-(((5-nitropyridin-2-yl)thio)selanyl)-1-oxopropan-2-yl)-N₂-(tert-butoxycarbonyl)-L-glutaminate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With rose bengal In acetonitrile for 1h; Irradiation;

Reference： [1]Arsenyan, Pavel; Dimitrijevs, Pavels; Lapcinska, Sindija [Advanced Synthesis and Catalysis, 2021, vol. 363, # 16, p. 3968 - 3972]

77
[ 2127-09-5 ]
benzyl (tert-butoxycarbonyl)-L-cysteinylglycinate [ No CAS ]
benzyl N-(tert-butoxycarbonyl)-S-((5-nitropyridin-2-yl)thio)-L-cysteinylglycinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With rose bengal In acetonitrile for 1h; Irradiation;

Reference： [1]Arsenyan, Pavel; Dimitrijevs, Pavels; Lapcinska, Sindija [Advanced Synthesis and Catalysis, 2021, vol. 363, # 16, p. 3968 - 3972]

78
[ 2127-09-5 ]
tert-butyl N<SUP>5</SUP>-((R)-1-((2-(benzyloxy)-2-oxoethyl)amino)-3-mercapto-1-oxopropan-2-yl)-N<SUP>2</SUP>-(tert-butoxycarbonyl)-L-glutaminate [ No CAS ]
tert-butyl N₅-((R)-1-((2-(benzyloxy)-2-oxoethyl)amino)-3-((5-nitropyridin-2-yl)disulfaneyl)-1-oxopropan-2-yl)-N₂-(tert-butoxycarbonyl)-L-glutaminate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With rose bengal In acetonitrile for 1h; Irradiation;

Reference： [1]Arsenyan, Pavel; Dimitrijevs, Pavels; Lapcinska, Sindija [Advanced Synthesis and Catalysis, 2021, vol. 363, # 16, p. 3968 - 3972]

79
[ 2127-10-8 ]
[ 2127-09-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness

	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: ammonium bicarbonate / acetonitrile; water / 1.5 h / 20 °C / pH 8.0 / Darkness

Reference： [1]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[2]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[3]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[4]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[5]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[6]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[7]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[8]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[9]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[10]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[11]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[12]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[13]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[14]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[15]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[16]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]
[17]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]

80
[ 2127-10-8 ]
[ 100-53-8 ]
[ 2127-09-5 ]
2-(benzyldisulfaneyl)-5-nitropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid In dichloromethane at 20℃; for 2h;

Reference： [1]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]

81
[ 107-03-9 ]
[ 2127-10-8 ]
[ 2127-09-5 ]
C₈H₁₀N₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid In dichloromethane at 20℃; for 2h;

Reference： [1]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]

82
[ 109-79-5 ]
[ 2127-10-8 ]
[ 2127-09-5 ]
C₉H₁₂N₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With trifluoroacetic acid In dichloromethane at 20℃; for 2h;

Reference： [1]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]

83
[ 2127-10-8 ]
[ 541-31-1 ]
[ 2127-09-5 ]
C₁₀H₁₄N₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid In dichloromethane at 20℃; for 2h;

Reference： [1]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]

84
2-methyl-1-butanethiol [ No CAS ]
[ 2127-10-8 ]
[ 2127-09-5 ]
C₁₀H₁₄N₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid In dichloromethane at 20℃; for 2h;

Reference： [1]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]

85
[ 2127-10-8 ]
[ 156-57-0 ]
[ 2127-09-5 ]
2-(5-nitro-pyridin-2-yldisulfanyl)-ethylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid In dichloromethane at 20℃; for 2h;

Reference： [1]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]

86
[ 2127-10-8 ]
[ 60-24-2 ]
[ 2127-09-5 ]
2-(2-(5-nitropyridin-2-yl)disulfanyl)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid In dichloromethane at 20℃; for 2h;

Reference： [1]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]

87
[ 1569-69-3 ]
[ 2127-10-8 ]
[ 2127-09-5 ]
C₁₁H₁₄N₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid In dichloromethane at 20℃; for 2h;

Reference： [1]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]

88
[ 1679-07-8 ]
[ 2127-10-8 ]
[ 2127-09-5 ]
C₁₀H₁₂N₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid In dichloromethane at 20℃; for 2h;

Reference： [1]Arora, Paramjit S.; Marrone, Frank; Modell, Ashley E.; Panigrahi, Nihar R.; Zhang, Yingkai [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1198 - 1204]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	2127-09-5	MDL No. :	MFCD00030890
Formula :	C₅H₄N₂O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BHQUBONFIYNJDA-UHFFFAOYSA-N
M.W :	156.16	Pubchem ID :	2763652
Synonyms :

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.31
TPSA :	97.51 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.2 cm/s

Log Po/w (iLOGP) :	1.19
Log Po/w (XLOGP3) :	1.48
Log Po/w (WLOGP) :	1.28
Log Po/w (MLOGP) :	0.3
Log Po/w (SILICOS-IT) :	-0.45
Consensus Log Po/w :	0.76

[ CAS No. 2127-09-5 ] {[proInfo.proName]}

Quality Control of [ 2127-09-5 ]

Related Doc. of [ 2127-09-5 ]

Product Details of [ 2127-09-5 ]

Calculated chemistry of [ 2127-09-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2127-09-5 ]

Application In Synthesis of [ 2127-09-5 ]

[ 2127-09-5 ] Synthesis Path-Upstream 1~1

[ 2127-09-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 2127-09-5 ]

Nitroes

Related Parent Nucleus of
[ 2127-09-5 ]

Thiophenols

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.12
Solubility :	1.19 mg/ml ; 0.00761 mol/l
Class :	Soluble
Log S (Ali) :	-3.13
Solubility :	0.115 mg/ml ; 0.000733 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.5
Solubility :	4.92 mg/ml ; 0.0315 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.96

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 2127-09-5 ] {[proInfo.proName]}

Quality Control of [ 2127-09-5 ]

Related Doc. of [ 2127-09-5 ]

Product Details of [ 2127-09-5 ]

Calculated chemistry of [ 2127-09-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2127-09-5 ]

Application In Synthesis of [ 2127-09-5 ]

[ 2127-09-5 ] Synthesis Path-Upstream 1~1

[ 2127-09-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 2127-09-5 ]

Nitroes

Related Parent Nucleus of [ 2127-09-5 ]

Thiophenols

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2127-09-5 ]

Related Parent Nucleus of
[ 2127-09-5 ]