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Product Details of [ 105-34-0 ]

CAS No. :105-34-0 MDL No. :MFCD00001939
Formula : C4H5NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ANGDWNBGPBMQHW-UHFFFAOYSA-N
M.W : 99.09 Pubchem ID :7747
Synonyms :

Calculated chemistry of [ 105-34-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 22.38
TPSA : 50.09 Ų

Pharmacokinetics

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) : -7.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.99
Log Po/w (XLOGP3) : -0.47
Log Po/w (WLOGP) : 0.07
Log Po/w (MLOGP) : -0.5
Log Po/w (SILICOS-IT) : -0.05
Consensus Log Po/w : 0.01

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.03
Solubility : 93.3 mg/ml ; 0.941 mol/l
Class : Very soluble
Log S (Ali) : -0.12
Solubility : 76.0 mg/ml ; 0.767 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.37
Solubility : 42.6 mg/ml ; 0.43 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.4

Safety of [ 105-34-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P305+P351+P338-P337+P313 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 105-34-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 105-34-0 ]
  • Downstream synthetic route of [ 105-34-0 ]

[ 105-34-0 ] Synthesis Path-Upstream   1~50

  • 1
  • [ 105-34-0 ]
  • [ 927-63-9 ]
  • [ 40134-18-7 ]
YieldReaction ConditionsOperation in experiment
93.9%
Stage #1: at 140℃; for 1 h; Microwave irradiation
In a reactor, 59 mL (0.5 mol) of methyl cyanoacetate was added to the reactor,N-ethylpyridine tetrafluoroborate 50 mL,3-dimethylaminopropenal 62 mL (0.5 mol) was homogeneously mixed,Microwave heating to 140 temperature and heat for 1h to carry out the reaction, TLC detection (oilEther: methylene chloride 1: 2 developed, sublimed iodine color)3-dimethylaminopropenal reaction completely, cooled to room temperature, organic solvent BEther 60mL extraction 3 times, residual phase ion water washing vacuum drying after repeated use, organic phase into the dry HCl gas, HPLC withThe reaction is continued until the reaction ends. Add the mass fraction of 20percent sodium hydroxide solution to adjust the pH = 5-6, separated, the water layer with ether20mL × 3 times extraction, combined organic layer, washed with water, molecular sieve drying, filtration, evaporation of solvent ether recovery, the residue byThe product was distilled at 110-115 ° C / 1 mmHg to prepare methyl 2-chloronicotinate and 80.6 g of colorless liquid in a yield of 93.9percent.
Reference: [1] Patent: CN105001154, 2017, B, . Location in patent: Paragraph 0060; 0061; 0062
  • 2
  • [ 63270-91-7 ]
  • [ 105-34-0 ]
  • [ 40134-18-7 ]
YieldReaction ConditionsOperation in experiment
92.7%
Stage #1: at 60℃; Sonication
Stage #2: at 60℃; for 0.833333 h; Sonication
In a 500 mL three-necked flask equipped with a thermometer, 69 mL (0.5 mol) of N,N-dibutylaminocrolein and K2CO3 5.0 g were added first, and then methyl cyanoacetate (65 mL (0.6 mol)) was added to prepare. A good device is placed in the sonicator. Ultrasonic radiation conditions were set, and the reaction was carried out at a temperature of 60°C, an ultrasonic power of 300 W, and a frequency of 100 KHz TLC test (petroleum ether:dichloromethane 1:2 development, sublimation iodine development) N,N-dibutylene Amine acrolein reaction is complete. After that, HCl gas was again introduced, the ultrasonic radiation was the same as above, and the reaction was for about 50 min. The reaction was followed by HPLC until the reaction was completed. After the reaction is completed, add sodium carbonate solution to adjust pΗ = 5-6, and separate the liquid. The aqueous layer is extracted with ethyl acetate 20 mL×3. The organic layers are combined, and the organic layer is washed with deionized water (10 mL). The organic layer is dried overnight and filtered. The solvent was evaporated by heating and the residue was distilled under reduced pressure. The 110-115 °C/lmmHg fraction was collected to obtain methyl 2-chloronicotinate, 79.5 g of a colorless liquid, and the yield was 92.7percent.
Reference: [1] Patent: CN104945317, 2018, B, . Location in patent: Paragraph 0057; 0058; 0061
  • 3
  • [ 13070-22-9 ]
  • [ 105-34-0 ]
  • [ 52718-95-3 ]
YieldReaction ConditionsOperation in experiment
90.5%
Stage #1: With potassium hydrogencarbonate In ethanol at 60℃; Sonication
Stage #2: With hydrogen bromide In ethanol at 60℃; for 0.583333 h; Sonication
In a 500 mL three-necked flask equipped with a thermometer, 61 mL (0.5 mol) of 3-diethylaminopropylene, 50 mL of a 95percent ethanol, and KHCO3 5.0 g were added first, followed by 65 mL of methyl cyanoacetate (0.6percent). Mol). Place the prepared device in the sonicator. Ultrasonic radiation conditions were set, and the reaction was carried out at a temperature of 60 °C, an ultrasonic power of 250 W, and a frequency of 150 ΚΗz. TLC test (petroleum ether: dichloromethane 1:2 development, sublimation iodine development) 3-diethylamino Acrolein reaction is complete. After that, HBr gas was introduced, the ultrasonic irradiation conditions were the same as above, the reaction was for about 35 minutes, and the reaction was followed by HPLC until the reaction was completed. After the end of the reaction, 10percent potassium hydroxide solution was added to adjust ρΗ=5-6, and the layers were separated. The aqueous layer was extracted with ethyl acetate 20 mL×3 times, and the organic layers were combined. The deionized water was washed with 10 mL water and the organic layer was sieved. The mixture was dried overnight, filtered, and the solvent was removed under reduced pressure to obtain methyl 2-bromonicotinate as a light brown liquid (97.7 g). The yield was 90.5percent.
Reference: [1] Patent: CN104945317, 2018, B, . Location in patent: Paragraph 0065; 0067; 0068
  • 4
  • [ 105-34-0 ]
  • [ 598-50-5 ]
  • [ 2434-53-9 ]
Reference: [1] Chemicke Zvesti, 1952, vol. 6, p. 357[2] Chem.Abstr., 1954, p. 7019
  • 5
  • [ 96-31-1 ]
  • [ 105-34-0 ]
  • [ 6642-31-5 ]
Reference: [1] Chemicke Zvesti, 1952, vol. 6, p. 357[2] Chem.Abstr., 1954, p. 7019
  • 6
  • [ 14080-32-1 ]
  • [ 105-34-0 ]
  • [ 88312-64-5 ]
Reference: [1] Recueil: Journal of the Royal Netherlands Chemical Society, 1983, vol. 102, # 7-8, p. 373 - 377
[2] Recueil: Journal of the Royal Netherlands Chemical Society, 1983, vol. 102, # 7-8, p. 373 - 377
[3] Recueil: Journal of the Royal Netherlands Chemical Society, 1983, vol. 102, # 7-8, p. 373 - 377
  • 7
  • [ 506-93-4 ]
  • [ 105-34-0 ]
  • [ 56-06-4 ]
Reference: [1] Patent: CN104109163, 2016, B, . Location in patent: Paragraph 0017
  • 8
  • [ 4760-34-3 ]
  • [ 105-34-0 ]
  • [ 2735-62-8 ]
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[2] Patent: TW2016/34463, 2016, A, . Location in patent: Paragraph 0090
  • 9
  • [ 67-56-1 ]
  • [ 372-09-8 ]
  • [ 105-34-0 ]
YieldReaction ConditionsOperation in experiment
97% at 70℃; for 20 h; General procedure: The mixture of carboxylic acid, alcohol and N-bromosuccinimide was stirred in a 25 mL reactortube at 70 °C for 2–40 h. After the completion of the reaction, the mixture was cooled to roomtemperature and alcohol was evaporated under reduced pressure. The isolation procedure was as follows, except where noted differently in Section 3.2.6. The residue was dissolved in ethyl acetate andconsecutively washed with 10 mL of 10percent Na2S2O3 (aq), 5 mL of saturated NaHCO3 (aq) and 10 mL ofdistilled water. The water phase was extracted with ethyl acetate (3Χ5 mL). The organic layers were combined, dried over Na2SO4 and the solvent was evaporated under reduced pressure.
Reference: [1] Synthesis, 1980, # 7, p. 547 - 551
[2] Molecules, 2018, vol. 23, # 9,
[3] Synthetic Communications, 1988, vol. 18, # 8, p. 847 - 854
[4] Patent: US2553065, 1949, ,
[5] Tetrahedron Letters, 1998, vol. 39, # 47, p. 8563 - 8566
[6] Journal of the American Chemical Society, 2005, vol. 127, # 27, p. 9674 - 9675
[7] Bioorganic Chemistry, 2004, vol. 32, # 4, p. 274 - 289
[8] Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 13, p. 5242 - 5246
[9] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 5, p. 2730 - 2735
[10] Tetrahedron, 2011, vol. 67, # 30, p. 5507 - 5515
  • 10
  • [ 110-67-8 ]
  • [ 105-34-0 ]
Reference: [1] Patent: US6700010, 2004, B1, . Location in patent: Page column 2
  • 11
  • [ 3154-54-9 ]
  • [ 105-34-0 ]
Reference: [1] Patent: WO2012/109164, 2012, A1, . Location in patent: Page/Page column 56
  • 12
  • [ 67-56-1 ]
  • [ 105-56-6 ]
  • [ 105-34-0 ]
Reference: [1] Synlett, 2007, # 3, p. 491 - 493
[2] Organic Syntheses, 1987, vol. 65, p. 230 - 230
[3] Journal of the Scientific Research Institute, Tokyo, 1958, vol. 52, p. 105,110
[4] Tetrahedron Letters, 1980, vol. 21, p. 2857 - 2860
[5] Green Chemistry, 2012, vol. 14, # 8, p. 2273 - 2281
  • 13
  • [ 74-87-3 ]
  • [ 372-09-8 ]
  • [ 105-34-0 ]
Reference: [1] Patent: US6239307, 2001, B1,
  • 14
  • [ 67-56-1 ]
  • [ 107-91-5 ]
  • [ 105-34-0 ]
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, p. 5351 - 5353
  • 15
  • [ 35234-87-8 ]
  • [ 109-77-3 ]
  • [ 101342-43-2 ]
  • [ 105-34-0 ]
Reference: [1] Journal of the American Chemical Society, 1986, vol. 108, p. 4920
  • 16
  • [ 143-33-9 ]
  • [ 96-34-4 ]
  • [ 105-34-0 ]
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[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 23, p. 147
  • 17
  • [ 124-41-4 ]
  • [ 105-56-6 ]
  • [ 105-34-0 ]
Reference: [1] Patent: US2011/28741, 2011, A1, . Location in patent: Page/Page column 35
  • 18
  • [ 67-56-1 ]
  • [ 105-56-6 ]
  • [ 64-17-5 ]
  • [ 105-34-0 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 26, p. 8507 - 8514
  • 19
  • [ 67-56-1 ]
  • [ 10258-54-5 ]
  • [ 105-34-0 ]
Reference: [1] Helvetica Chimica Acta, 1982, vol. 65, # 4, p. 1197 - 1201
  • 20
  • [ 151-50-8 ]
  • [ 105-39-5 ]
  • [ 105-56-6 ]
  • [ 105-34-0 ]
Reference: [1] Journal of the American Chemical Society, 1904, vol. 26, p. 1545
[2] Bulletin of the Chemical Society of Japan, 1927, vol. 2, p. 143[3] Chem. Zentralbl., 1927, vol. 98, # II, p. 913
  • 21
  • [ 39687-95-1 ]
  • [ 105-34-0 ]
Reference: [1] Chemische Berichte, 1987, vol. 120, p. 1 - 4
[2] Journal of Organic Chemistry, 1987, vol. 52, # 4, p. 648 - 652
  • 22
  • [ 67-56-1 ]
  • [ 109-77-3 ]
  • [ 105-34-0 ]
  • [ 108-59-8 ]
Reference: [1] Synthetic Communications, 2003, vol. 33, # 19, p. 3461 - 3466
  • 23
  • [ 67-56-1 ]
  • [ 109-77-3 ]
  • [ 105-34-0 ]
Reference: [1] Synthetic Communications, 2006, vol. 36, # 19, p. 2883 - 2886
  • 24
  • [ 67-56-1 ]
  • [ 1071-36-9 ]
  • [ 105-34-0 ]
Reference: [1] Chemicke Zvesti, 1954, vol. 8, p. 76[2] Chem.Abstr., 1956, p. 177
[3] Chemicke Zvesti, 1954, vol. 8, p. 63,69-73[4] Chem.Abstr., 1955, p. 6094
  • 25
  • [ 7732-18-5 ]
  • [ 4540-33-4 ]
  • [ 16630-91-4 ]
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Reference: [1] Journal of the American Chemical Society, 1937, vol. 59, p. 2327,2329
  • 26
  • [ 7647-01-0 ]
  • [ 67-56-1 ]
  • [ 70138-31-7 ]
  • [ 105-34-0 ]
  • [ 108-59-8 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 47,52
  • 27
  • [ 122-51-0 ]
  • [ 105-34-0 ]
  • [ 29097-00-5 ]
Reference: [1] Bioorganic Chemistry, 2019, vol. 84, p. 226 - 238
  • 28
  • [ 4637-24-5 ]
  • [ 105-34-0 ]
  • [ 29097-00-5 ]
Reference: [1] Monatshefte fur Chemie, 2017, vol. 148, # 10, p. 1767 - 1780
  • 29
  • [ 74-89-5 ]
  • [ 105-34-0 ]
  • [ 6330-25-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 18, p. 7590 - 7599
[2] Helvetica Chimica Acta, 1998, vol. 81, # 7, p. 1319 - 1328
[3] Journal of Organic Chemistry, 2007, vol. 72, # 14, p. 5297 - 5312
  • 30
  • [ 62-53-3 ]
  • [ 105-34-0 ]
  • [ 621-03-4 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 11, p. 2884 - 2887
[2] Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1896 - 1907
[3] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1727 - 1736
[4] Justus Liebigs Annalen der Chemie, 1977, p. 1642 - 1660
[5] Journal of Organic Chemistry, 2007, vol. 72, # 14, p. 5297 - 5312
  • 31
  • [ 100-46-9 ]
  • [ 105-34-0 ]
  • [ 10412-93-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 18, p. 7590 - 7599
[2] Organic Letters, 2011, vol. 13, # 11, p. 2884 - 2887
[3] Patent: US5652250, 1997, A,
[4] Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1896 - 1907
[5] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1727 - 1736
[6] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 11, p. 3019 - 3026
[7] Chemistry - A European Journal, 2015, vol. 21, # 42, p. 14851 - 14861
  • 32
  • [ 40018-26-6 ]
  • [ 105-34-0 ]
  • [ 4651-81-4 ]
YieldReaction ConditionsOperation in experiment
94% With triethylamine; N,N-dimethyl-formamide In methanol at 50℃; for 0.05 h; Sealed tube; Microwave irradiation; Inert atmosphere To two 20 mL microwave pressure vials was each added 1,4-dithiane-2,5-diol (2.0 g, 13.1mmol, 1.0 eq.) and MeOH (10.5 mL), and the vials were sealed. Through the septa was addedmethylcyanoacetate (2.32 mL, 26.3 mmol, 2.0 eq.), Et3N (1.28 mL, 9.20 mmol, 0.7 eq.), andDMF (3 drops), and the reactions were heated via microwave irradiation at 50 °C for 3 min. Atrt, the precipitates were combined and collected by filtration and washed with cold MeOH to provide 16as a white solid (3.88 g, 24.7 mmol, 94percent).
86% With triethylamine In methanol at 0 - 40℃; Thienopyrimidine Methyl 2-aminothiophene-3-carboxylate (1). l,4-Dithiane-2,5-diol (312.8 g, 2.05 mol) was mixed with MeOH (1000 mL), and methyl cyanoacetate (304.05 g, 3.06 mol) was added while stirring at 0 °C. Then NEt3 (72.55 g, 0.72 mol) was added drop wise over 2.5 h at 0 °C. The reaction temperature was slowly increased to 40 °C over 1 h. and kept stirring. After cooling to rt, the mixture was filtered and the liquid fraction was concentrated. The concentrated oil was extracted with boiling pet. ether (bp. 60-80 °C) (10χ750 mL). The combined organic fraction was concentrated which gave a solid crystalline product. After drying this gave 408.2 g (86percent) of 1, mp. 78 - 80 °C Rf (CHC13) = 0.33; 1H NMR (400 MHz, DMSO-d6) δ: 7.24 (s br, 2H, NH2), 6.81 (d, J= 5.8, 1H), 6.27 (d, J= 5.8, 1H), 3.69 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ: 164.8, 164.0, 124.9, 106.5, 103.7, 50.5. IR (neat, cm"1): 3421, 3319, 1655, 1316, 1273, 676; HRMS (EI, 70 eV, m/z): 157.0201 (calcd C6H7N02S, 157.0198, M+).
78% With triethylamine In methanol at 0 - 60℃; The synthesis was carried out as described by Hallas and Towns.18   1,4-Dithiane-2,5-diol (15.0 g, 99.0 mmol) was mixed with   MeOH (30 mL), and   methyl cyanoacetate (16.3 g, 164 mmol) was added while stirring. Then   NEt3 (5.98 g, 59.1 mmol) was added dropwise over 10 min at 0 °C. The reaction temperature was slowly increased to 60 °C over 1 h, and kept stirring for 1 h. After cooling to rt, the mixture was filtered and the liquid fraction was concentrated and allowed to crystallise at −18 °C for 18 h. The solid formed was isolated, washed with n-heptane (3×50 mL) and dried to yield 20.1 g (128 mmol, 78percent) of   1 as a yellowish solid, mp. 72–73 °C, (lit.15 77–78 °C); Rf (CHCl3)=0.33; 1H NMR (400 MHz, DMSO-d6) δ: 7.24 (s br, 2H, NH2), 6.81 (d, J=5.8, 1H), 6.27 (d, J=5.8, 1H), 3.69 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ: 164.8, 164.0, 124.9, 106.5, 103.7, 50.5; IR (neat, cm−1): 3421, 3319, 1655, 1316, 1273, 676; HRMS (EI, 70 eV, m/z): 157.0201 (calcd C6H7NO2S, 157.0198, M+). The 1H NMR spectrum from CDCl3 corresponded with that reported by Huang et al.39
64% With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 3 h; Add in a 250 mL round bottom flask1,4-Dithio-2,5-diol (7.6 g, 50 mmol),Methyl cyanoacetate (9.9g, 100mmol) and 20mL DMF,The mixture was stirred at 0 °C.Triethylamine (3.6 g, 50 mmol) was gradually added dropwise to the reaction system.Stir at room temperature for 3 h.Quench with water, extract with methylene chloride, and remove the solvent on a rotary evaporator.Purification by column chromatography. White solid (11 g, 64percent) was obtained.
44% With triethylamine In methanol at 0 - 40℃; for 2.5 h; To a solution of methanol (35 g, 0.1 mol) in methyl cyanoacetate (10 g, 0.1 mol) and 1,4-dithiane-2,5-diol mL) was adjusted to 0°C and triethylamine (Et3N, 3.8 mL, 0.027 mol) was slowly added over 30 minutes and stirred at 40°C for 2 hours. The resulting solid was filtered and washed with diethyl ether to give compound 16 (7.014 g, 44percent) as a white solid.

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 1947 - 1953
[2] Patent: WO2015/959, 2015, A1, . Location in patent: Page/Page column 47
[3] Tetrahedron Letters, 2007, vol. 48, # 30, p. 5261 - 5264
[4] Tetrahedron, 2012, vol. 68, # 45, p. 9226 - 9233
[5] Patent: WO2005/63734, 2005, A2, . Location in patent: Page/Page column 60-61
[6] Patent: CN107573386, 2018, A, . Location in patent: Paragraph 0044-0047
[7] MedChemComm, 2015, vol. 6, # 2, p. 339 - 346
[8] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
[9] Chemical Biology and Drug Design, 2010, vol. 76, # 2, p. 116 - 129
[10] Patent: KR2017/92126, 2017, A, . Location in patent: Paragraph 0092-0096
[11] Patent: US5654307, 1997, A,
[12] Patent: US2007/99929, 2007, A1,
  • 33
  • [ 75-07-0 ]
  • [ 105-34-0 ]
  • [ 4651-81-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 9, p. 3620 - 3635
[2] European Journal of Medicinal Chemistry, 2019, vol. 161, p. 239 - 251
  • 34
  • [ 123-38-6 ]
  • [ 105-34-0 ]
  • [ 19369-53-0 ]
YieldReaction ConditionsOperation in experiment
73.6% With morpholine; sulfur In N,N-dimethyl-formamide at 50℃; The sulfur powder (960.0mg, 30.0mmol)In a single mouth bottle,Add DMF 5 mL,Were successively added methyl cyanoacetate (3.39g, 30.0mmol),Morpholine (1.48 g, 17.0 mmol),The reaction solution was dark brown,Propionaldehyde (1.74 g, 30.0 mmol) was added,50 ° C overnight.After completion of the reaction, the mixture was cooled to room temperature,Add appropriate amount of water,Ethyl acetate was extracted three times,The combined organic phases were washed with saturated brine,Dried over anhydrous magnesium sulfate,The crude product was distilled under reduced pressure.Separation and purification by column chromatography,To give a pale yellow solid.Yield: 73.6percent
33% for 12 h; Reflux; Inert atmosphere General procedure: A solution of aliphatic carbonyl compound 1 (2 mmol), activatednitrile (2 mol), elemental sulfur (2 mmol) and triethylamine(2 mmol) in MeOH (15 ml) was heated at reflux temperature for12 h under argon atmosphere. The MeOH was evaporated underreduced pressure and the residue was extracted with dichloromethane(3 50ml). The combined organic phases were washedwith a saturated solution of NaHCO3, dried over magnesium sulfateand the solvent was evaporated under reduced pressure. Purificationby column chromatography (silica, eluent CH2Cl2) afforded 3 asan off-white solid or a semi-solid.
Reference: [1] Patent: CN106167497, 2016, A, . Location in patent: Paragraph 0241; 0242; 0243
[2] ChemMedChem, 2018,
[3] European Journal of Medicinal Chemistry, 2017, vol. 132, p. 219 - 235
[4] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 305 - 308
[5] Patent: WO2013/190137, 2013, A2, . Location in patent: Page/Page column 73
[6] ChemMedChem, 2014, vol. 9, # 12, p. 2744 - 2753
[7] Patent: US2015/126559, 2015, A1, . Location in patent: Paragraph 0379; 0380
[8] European Journal of Medicinal Chemistry, 2019, vol. 161, p. 239 - 251
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  • [ 10467-10-4 ]
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  • [ 30414-53-0 ]
Reference: [1] Chemische Berichte, 1985, vol. 118, # 9, p. 4073 - 4085
  • 36
  • [ 105-34-0 ]
  • [ 74-88-4 ]
  • [ 72291-30-6 ]
YieldReaction ConditionsOperation in experiment
73% With potassium carbonate In acetone EXAMPLE 1
Synthesis of N-(N-4-amidinobenzoyl-α,α-dimethyl-β-alanyl)-4-piperidineacetic acid STR7 (1) Methyl 2,2-dimethyl-cyanoacetate
Methyl cyanoacetate (15 ml) and methyl iodide (200 g) were stirred and refluxed under the presence of potassium carbonate in acetone for 4 days and the potassuim carbonate was then removed by filtration.
Acetone was distilled off from the filtrate and the residue was distilled in vacuo (16 mmHg, 76° C.) to yield methyl 2,2-dimethyl-cyanoacetate (19.5 g, 73percent).
NMR: 1 H (270 MHz, CDCl3) 1.62, s, 6H: 3.83, s, 3H: 13 C(67.5 MHz, CDCl3) 24.6, 38.4, 121.0, 170.0
48%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.666667 h;
Stage #2: at 20℃; for 12 h;
NaH (15.5 g, 60percent dispersion in oil) was added portionwise over 10 min to the solution of ethyl cyanoacetate (20 g, 0.177 mol) in dry DMF (300 mL) at 0 °C.
The resulting reaction mixture was stirred at room temperature for 30 min and cooled again to 0 °C. Methyl iodide (28 mL, 0.44 mol) in THF (50 mL) was added dropwise and the reaction mixture was stirred at room temperature for 12 h, and then quenched with saturated NH4Cl solution.
The mixture was then diluted with EtOAc; the organic layer was washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford crude product that was purified by column chromatography (silica gel 60-120 mesh, eluent 5percent EtOAc in petroleum ether) to afford methyl 2-cyano-2-methylpropanoate (12 g, yield 48percent) as a pale yellow solid.
11 g With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 72 h; A mixture of cyano-acetic acid methyl ester (1 1 g, 11 1 mmol), CS2CO3 (108 g, 333 mmol) and methyl iodide (35 mL, 556 mmol) in anhydrous DMF (300 mL) was stirred at r.t. for 3 days. Brine (100 mL) and ether (250 mL) were added, and the aqueous layer was extracted with additional ether (250 mL). The organic layers were combined, washed with water (4 x 200 mL), and dried over MgSO/t. The solvent was evaporated to give 1 1 g of the title compound as a yellow oil. lH NMR (CDCI3, 200 MHz): 8ppm= 3.83 (s, 3H), 1.63 (s, 6H).
Reference: [1] Patent: US5866592, 1999, A,
[2] Patent: EP2533783, 2015, B1, . Location in patent: Paragraph 0551-0552
[3] Acta Chemica Scandinavica (1947-1973), 1968, vol. 22, # 8, p. 2453 - 2461
[4] Phosphorus and Sulfur and the Related Elements, 1987, vol. 32, p. 153 - 162
[5] Patent: WO2013/134660, 2013, A1, . Location in patent: Paragraph 0428
  • 37
  • [ 74-87-3 ]
  • [ 105-34-0 ]
  • [ 72291-30-6 ]
Reference: [1] Patent: WO2010/112482, 2010, A1, . Location in patent: Page/Page column 27
  • 38
  • [ 77-78-1 ]
  • [ 105-34-0 ]
  • [ 72291-30-6 ]
Reference: [1] Chemische Berichte, 1981, vol. 114, # 8, p. 2866 - 2883
  • 39
  • [ 96-34-4 ]
  • [ 105-34-0 ]
  • [ 6283-71-2 ]
Reference: [1] Liebigs Annalen der Chemie, 1983, # 1, p. 112 - 136
[2] Journal of the American Chemical Society, 1975, vol. 97, # 4, p. 800 - 807
  • 40
  • [ 89-98-5 ]
  • [ 105-34-0 ]
  • [ 7315-17-5 ]
Reference: [1] ChemCatChem, 2015, vol. 7, # 17, p. 2590 - 2593
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7693 - 7701
  • 41
  • [ 109-89-7 ]
  • [ 105-34-0 ]
  • [ 26391-06-0 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 78, p. 10792 - 10795
  • 42
  • [ 105-34-0 ]
  • [ 51513-29-2 ]
Reference: [1] Synthesis, 1974, p. 574 - 575
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 4, p. 1036 - 1040
[3] Organometallics, 2013, vol. 32, # 13, p. 3744 - 3752
  • 43
  • [ 86-57-7 ]
  • [ 105-34-0 ]
  • [ 3100-67-2 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With potassium cyanide; potassium hydroxide In N,N-dimethyl-formamide at 10℃; for 0.333333 h; Inert atmosphere
Stage #2: at 60℃; for 4 h;
The dried 2 L reactor to nitrogen under ethyl cyanoacetate 139.8 g (1.236 mol), potassium cyanide 29.5 g (0.453 mol), potassium hydroxide 46.2 g (0.824 mol), dimethylformamide 920 mL dissolved after 10 in the mixture was stirred for 20 minutes. Then into a 1-nitro-naphthalene 92 g (412 mol) to the reaction and stirred for 4 hours at 60 . After the reaction solvent was concentrated into a 10percent sodium hydroxide aqueous solution 600 mL is stirred at reflux for 1 hour. The solid was filtered by a column chromatography with methylene chloride and heptane to give the compound 50 g (yield: 60percent) represented by Formula 3-a].
60%
Stage #1: With potassium cyanide; potassium hydroxide In N,N-dimethyl-formamide at 10℃; for 0.333333 h;
Stage #2: at 60℃; for 4 h;
A dried 2 L reactor was charged with 139.8 g (1.236 mol) of methyl cyanoacetate, 29.5 g (0.453 mol) of potassium cyanide, 46.2 g (0.824 mol) of potassium hydroxide, dissolve in 920 mL of dimethylformamide and stir at 10 °C for 20 minutes. 92 g (412 mol) of 1-nitronaphthalene is then added to the reaction mixture and stirred at 60 ° C for 4 hours.After completion of the reaction, the solvent is concentrated, 600 mL of a 10percent sodium hydroxide aqueous solution is added, and the mixture is refluxed with stirring for 1 hour.The solid was filtered and subjected to column chromatography with methylene chloride and heptane to obtain 50 g (yield 60percent) of the compound represented by [Intermediate 3-a].
54% With potassium cyanide; potassium hydroxide In N,N-dimethyl-formamide at 60℃; 1-nitro-naphthalene 97 g (0.56 mol), methyl cyanoacetate 166.5 g (1.68 mol), potassium cyanide, 40.1 g (0.62 mol) into potassium hydroxide 62.9 g (1.12 mol) was stirred. Then add 970 mL of dimethylformamide was stirred overnight at 60° C . After concentrated under reduced pressure to remove the solvent at room temperature and add 500 mL 10percent aqueous sodium hydroxide solution was refluxed for about one hour. After extracted with ethyl acetate and then separated by column chromatography it was recrystallized from toluene and heptane to obtain <9-a> 50.8 g (yield: 54percent).
54% With potassium cyanide; potassium hydroxide In N,N-dimethyl-formamide at 60℃; 1-nitro-naphthalene (97 g, 0.56 mol), methyl cyanoacetate (166.5 g, 1.68 mol), potassium cyanide (40.1 g, 0.62mol), potassium hydroxide (62.9 g, 1.12 mol) and dissolved in dimethylformamide (970 mL) and the mixture was stirred overnight at 60°C. After concentrated under reduced pressure to remove the solvent at room temperature into a 500 mL 10percent aqueous sodium hydroxide solution was refluxed for about one hour. After extraction with ethyl acetate and separated by column chromatography and recrystallized from toluene-heptane to give the Sub 2-2-1 50.8 g (yield: 54percent).
54% With potassium cyanide; potassium hydroxide In N,N-dimethyl-formamide at 60℃; 97 g (0.56 mol) of 1-nitronaphthalene,166.5 g (1.68 mol) of methyl cyanoacetate,40.1 g (0.62 mol) of potassium cyanide,62.9 g (1.12 mol) of potassium hydroxide,And the mixture was stirred.Dimethylformamide 970 mLAnd the mixture was stirred overnight at 60 ° C.After the solvent was removed by concentration under reduced pressure at room temperature, 10percent500 mL of an aqueous solution of sodium hydroxide was added and the mixture was refluxed for about 1 hour.After separation by column chromatography, recrystallization from toluene and heptane gave 50.8 g of intermediate 4-a. (Yield: 54percent)

Reference: [1] Patent: KR2015/145463, 2015, A, . Location in patent: Paragraph 0302-0305
[2] Patent: KR2016/36162, 2016, A, . Location in patent: Paragraph 0249-0251
[3] Patent: KR101554545, 2015, B1, . Location in patent: Paragraph 0447-0453
[4] Patent: KR101604647, 2016, B1, . Location in patent: Paragraph 0145; 0147; 0148
[5] Patent: KR2018/10087, 2018, A, . Location in patent: Paragraph 0460-0464
  • 44
  • [ 86-57-7 ]
  • [ 105-34-0 ]
  • [ 3100-67-2 ]
YieldReaction ConditionsOperation in experiment
75% With potassium hydroxide In N,N-dimethyl-formamide at 60℃; In a reactor, 1-nitronaphthalene (97 g, 0.56 mol), methyl cyanoacetate (166.5 g, 1.68 mol), potassium cyanide (40.1 g, 0.62 mol), and potassium hydroxide (62.9 g, 1.12 mol) were stirred together. To the reactants was added dimethylformamide (970 mL), followed by stirring at 60° C. overnight. The solvent was removed by vacuum concentration at room temperature, after which a 10percent sodium hydroxide solution (500 mL) was added and refluxed for about 1 hr. Recrystallization in toluene and heptane subsequent to separation through column chromatography afforded [Intermediate 7-a] (50.8 g): yield 75percent.
Reference: [1] Patent: US2018/233669, 2018, A1, . Location in patent: Paragraph 0262-0263
  • 45
  • [ 78-93-3 ]
  • [ 105-34-0 ]
  • [ 4651-93-8 ]
YieldReaction ConditionsOperation in experiment
40.7% With morpholine; sulfur In N,N-dimethyl-formamide at 50℃; The sulfur powder (160.0mg, 5.0mmol) to a single-neck flask,Add DMF 1.5 mL,Were successively added methyl cyanoacetate (495.4mg, 5.0mmol),Morpholine (435.6 mg, 5.0 mmol),The reaction solution was dark brown,2-butanone (901.4 mg, 12.5 mmol) was added,50 ° C overnight.After completion of the reaction, the mixture was cooled to room temperature,Add appropriate amount of water,Ethyl acetate was extracted three times,The combined organic phases were washed with saturated brine,Dried over anhydrous magnesium sulfate,The crude product was distilled under reduced pressure.Separation and purification by column chromatography,To give a pale yellow solid.Yield: 40.7percent
Reference: [1] Patent: CN106167497, 2016, A, . Location in patent: Paragraph 0414; 0415; 0416
[2] ChemMedChem, 2018,
[3] European Journal of Medicinal Chemistry, 2019, vol. 161, p. 239 - 251
  • 46
  • [ 108-94-1 ]
  • [ 105-34-0 ]
  • [ 108354-78-5 ]
YieldReaction ConditionsOperation in experiment
82% With morpholine; sulfur In ethanol for 3 h; Reflux Synthesis of compounds 1, 2a-i and 3a-i
Compound 1 was prepared through standard Gewald reaction.
14
4.4 g (0.05 mol) of morpholine was added dropwise into a stirred solution of cyclohexanone (4.91 g, 0.05 mol), methyl cyanoacetate (4.95 g, 0.05 mol) and sulfur (1.92 g, 0.06 mol) in 35 mL ethanol.
On completion, the mixture was refluxed for further 3 h.
After cooling to room temperature, the precipitate was separated by filtration and recrystallized from ethanol to give 1 as pale yellow powders (8.6 g, 82percent yield), mp 128.2-129.4 °C (lit.
15
128-130 °C), MS (GC-MS): m/z, 211 [M+H]+, 179, 151, 125, 91, 77, 65, 53.
70% With sulfur; triethylamine In ethanol at 20℃; Inert atmosphere To EtOH (37.5 mL) in an open flask was added S8 (4.68 g, 150 mmol, 1.0 eq.),cyclohexanone (23.3 mL, 225 mmol, 1.5 eq.), methyl cyanoacetate (13.3. mL, 150 mmol,1.0 eq.), and Et3N (10.4 mL, 75 mmol, 0.5 eq.), and the reaction was stirred at rt overnight.The flask was cooled to 0 °C with no stirring for 5 h followed by collection of theprecipitate by filtration. The solid was washed with ice cold EtOH then dried at rt overnight to yield 6a asan off-white solid (22.1 g, 105 mmol, 70percent)
20%
Stage #1: With diethylamine In ethanol for 0.166667 h; Reflux
Stage #2: With sulfur In ethanol for 3 h; Reflux
EXAMPLE 11; The reaction scheme for the synthesis of azo dye 11 is shown below. In a Gewald reaction, diethylamine (8 ml) was added to a solution of equimolar quantities of cyclohexanone (9.80 g, 0.10 mol) and methyl cyanoacetate (9.90 g, 0.10 mol) in ethanol, and the mixture was refluxed for 10 minutes. Then sulfur (3.53 g, 0.11 mol) was added, and the solution was refluxed for a further 3 hours. The pale yellow precipitate that formed was filtered and washed with cooled ethanol to give 11a as a pale yellow powder (4.22 g, 20percent yield), m.p. 132-133° C.
Reference: [1] Asian Journal of Chemistry, 2010, vol. 22, # 9, p. 7399 - 7404
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 12, p. 1942 - 1956
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 8, p. 1866 - 1871
[4] Tetrahedron, 2006, vol. 62, # 29, p. 7121 - 7131
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 1947 - 1953
[6] Chemical Biology and Drug Design, 2010, vol. 76, # 2, p. 116 - 129
[7] ChemMedChem, 2015, vol. 10, # 1, p. 69 - 82
[8] Patent: US2010/81823, 2010, A1, . Location in patent: Page/Page column 8
[9] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 305 - 308
[10] Journal of Medicinal Chemistry, 2013, vol. 56, # 9, p. 3620 - 3635
[11] Transition Metal Chemistry, 2014, vol. 39, # 4, p. 431 - 442
[12] Synlett, 2014, vol. 25, # 9,
[13] Journal of Molecular Liquids, 2017, vol. 243, p. 85 - 90
[14] Patent: WO2003/101979, 2003, A1, . Location in patent: Page 19
[15] European Journal of Medicinal Chemistry, 2019, vol. 161, p. 239 - 251
  • 47
  • [ 10544-50-0 ]
  • [ 108-94-1 ]
  • [ 105-34-0 ]
  • [ 108354-78-5 ]
Reference: [1] Synlett, 2014, vol. 25, # 20, p. 2918 - 2922
  • 48
  • [ 105-34-0 ]
  • [ 159635-50-4 ]
  • [ 362703-34-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 10, p. 2699 - 2704
  • 49
  • [ 105942-08-3 ]
  • [ 105-34-0 ]
  • [ 925672-88-4 ]
YieldReaction ConditionsOperation in experiment
78%
Stage #1: With sodium hydride In dimethyl sulfoxide at 0 - 20℃; for 0.5 h;
Stage #2: at 90℃;
4-Bromo-2-(cyanomethyl)benzonitrile. Sodium hydride (47.2 g, 1.18 mol) was suspended in 320 mL DMSO and cooled to 0°C in an ice-water bath. The mixture became viscous as the DMSO began to freeze. Methyl cyanoacetate (104 mL, 1.18 mol) was added slowly causing a slight temperature increase and thus a more easily stirrable solution. The mixture was stirred for 30 minutes at room temperature. 4- Bromo-2-fluorobenzonitrile (118 g, 590 mmol)(commercially available from Acros Organics (Order Number 29049)) was added via cannula as a solution in 500 mL DMSO. <n="191"/>The mixture was heated to an internal temperature of 90°C. The mixture was cooled and allowed to stand overnight. 1.2 L of water was added to the reaction mixture. The mixture was heated to an internal temperature of 104°C over 3 hours. 2.3 L of water were added, and the mixture was heated at reflux 16 hours. The mixture was cooled to 5°C. HCl (700 mL, 0.2 N) was added, and the mixture was allowed to stir at 5°C for 30 minutes. The resulting precipitate was filtered, washed with water, and dried to provide the product (102 g, 78 percent). LCMS (API-ES) m/z: 223, 221 (IVH-H+).
78%
Stage #1: With sodium hydride In dimethyl sulfoxide at 0 - 20℃; for 0.5 h;
Stage #2: at 90℃;
[00341] 4-Bromo-2-(cyanomethyl)benzonitrile: Sodium hydride (47.2 g, 1.18 mol) was suspended in 320 mL DMSO and cooled to O0C in an ice-water bath. The mixture became viscous as the DMSO began to freeze. Methyl cyanoacetate (104 mL, 1.18 mol) was added slowly causing a slight temperature increase and thus a more easily stirrable solution. The mixture was stirred for 30 minutes at room temperature. A- Bromo-2-fluorobenzonitrile (1 18 g, 590 mmol) (commercially available from Acros Organics (Order Number 29049)) was added via cannula as a solution in 500 mL DMSO. The mixture was heated to an internal temperature of 9O0C. The mixture was cooled and allowed to stand overnight. 1.2 L of water was added to the reaction mixture. The mixture was heated to an internal temperature of 1040C over 3 hours. 2.3 L of water was added and the mixture was heated at reflux 16 hours. The mixture was cooled to 50C and 700 mL of 0.2N HCl was added. The mixture was allowed to stir at 50C for 30 minutes. The resulting precipitate was filtered, washed with water, and dried to provide the product (102 g, 78 percent). LCMS (API-ES) m/z: 223, 221 (M+I-T).
78%
Stage #1: With sodium hydride In dimethyl sulfoxide at 0 - 30℃;
Stage #2: at 20 - 90℃;
Stage #3: With water In dimethyl sulfoxide at 104℃; Reflux
4-Bromo-2-(cyanomethyl)benzonitrile: NaH (47.2 g, 1.18 mol, Aldrich) was suspended in DMSO (320 mL) and cooled to O 0C in an ice-water bath. The mixture became viscous as the DMSO froze. Methyl cyanoacetate (104 mL, 1.18 mol, Aldrich) was added slowly causing a slight temperature increase and thus a more easily stirred solution. The internal temperature stayed below 30 0C. The mixture was stirred for 30 minutes at room temperature before 4-bromo-2-fluorobenzonitrile (118.0 g, 590 mmol, 3B Scientific Corporation Product List 3B3-007315) was added via cannula as a solution in DMSO (500 mL). The mixture was heated with a heating mantle to an internal temperature of 90 0C. Upon reaching 90 0C, the reaction was shown to be complete by LCMS. The mixture was allowed to stand at room temperature for 16 hours. Water (1.2 L) was added, and the temperature was then brought up slowly to an internal temperature of 104 0C. Water (2.3 L) was added and the mixture was heated at reflux for 20 hours. The mixture was cooled to 5 0C. HCl (700 mL, 0.2 N) was then added quickly, and the resulting mixture was stirred at 5 0C for about 30 minutes. The resulting precipitate was filtered, washed with water, and dried to afford 4-bromo-2-(cyanomethyl)benzonitrile (102 g, 78 percent).
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 3, p. 487 - 489
[2] Patent: WO2009/11871, 2009, A2, . Location in patent: Page/Page column 188-189
[3] Patent: WO2009/11880, 2009, A2, . Location in patent: Page/Page column 159
[4] Patent: WO2010/83246, 2010, A1, . Location in patent: Page/Page column 54-55
[5] Journal of Organic Chemistry, 2018, vol. 83, # 17, p. 9682 - 9695
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Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 3, p. 487 - 489
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