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[ CAS No. 13091-23-1 ] {[proInfo.proName]}

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Product Details of [ 13091-23-1 ]

CAS No. :13091-23-1 MDL No. :MFCD02683025
Formula : C5H3ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :JOTRPRKONYTVBV-UHFFFAOYSA-N
M.W :158.54 Pubchem ID :2735781
Synonyms :

Calculated chemistry of [ 13091-23-1 ]

Physicochemical Properties

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 : 38.07
TPSA : 58.71 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.92
Log Po/w (XLOGP3) : 1.31
Log Po/w (WLOGP) : 1.64
Log Po/w (MLOGP) : -0.13
Log Po/w (SILICOS-IT) : -0.09
Consensus Log Po/w : 0.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.49 mg/ml ; 0.00941 mol/l
Class : Soluble
Log S (Ali) : -2.14
Solubility : 1.14 mg/ml ; 0.00719 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.01
Solubility : 1.55 mg/ml ; 0.00979 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 13091-23-1 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P280-P301+P310-P305+P351+P338 UN#:2923
Hazard Statements:H301-H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 13091-23-1 ]

* 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 [ 13091-23-1 ]
  • Downstream synthetic route of [ 13091-23-1 ]

[ 13091-23-1 ] Synthesis Path-Upstream   1~40

  • 1
  • [ 13091-23-1 ]
  • [ 1839-17-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 563 - 566
[2] Patent: WO2011/130661, 2011, A1,
[3] Patent: WO2015/153683, 2015, A1,
  • 2
  • [ 64-17-5 ]
  • [ 13091-23-1 ]
  • [ 1796-84-5 ]
Reference: [1] Heterocycles, 2005, vol. 65, # 11, p. 2619 - 2634
[2] Journal of Medicinal Chemistry, 1985, vol. 28, # 4, p. 467 - 471
  • 3
  • [ 141-52-6 ]
  • [ 13091-23-1 ]
  • [ 1796-84-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1937, vol. 529, p. 291
[2] Chemische Berichte, 1927, vol. 60, p. 2108
[3] Chemische Berichte, 1924, vol. 57, p. 1188
  • 4
  • [ 13091-23-1 ]
  • [ 20511-15-3 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 1, p. 51 - 54
[2] Journal of the American Chemical Society, 2015, vol. 137, # 24, p. 7552 - 7555
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 4, p. 519 - 525
  • 5
  • [ 13091-23-1 ]
  • [ 273-75-6 ]
Reference: [1] Zhurnal Obshchei Khimii, 1956, vol. 26, p. 613,617; engl. Ausg. S. 663, 665
[2] Patent: CN108373476, 2018, A,
  • 6
  • [ 15014-25-2 ]
  • [ 13091-23-1 ]
  • [ 5832-44-0 ]
  • [ 5435-54-1 ]
Reference: [1] Synthetic Communications, 1981, vol. 11, # 9, p. 743 - 750
  • 7
  • [ 13091-23-1 ]
  • [ 33544-42-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 11, p. 2474 - 2485
[2] Chemische Berichte, 1924, vol. 57, p. 1188
[3] Chemical Communications, 2011, vol. 47, # 13, p. 4022 - 4024
[4] Russian Journal of Bioorganic Chemistry, 2015, vol. 41, # 4, p. 402 - 408[5] Bioorg. Khim., 2015, vol. 41, # 4, p. 454 - 461,8
  • 8
  • [ 13091-23-1 ]
  • [ 1681-37-4 ]
Reference: [1] Patent: US5262415, 1993, A,
[2] Patent: US5371086, 1994, A,
[3] Justus Liebigs Annalen der Chemie, 1937, vol. 529, p. 291
[4] Chemische Berichte, 1924, vol. 57, p. 1188
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 5023 - 5026
  • 9
  • [ 13091-23-1 ]
  • [ 1681-37-4 ]
  • [ 6980-08-1 ]
  • [ 40497-64-1 ]
  • [ 24484-96-6 ]
Reference: [1] Liebigs Annalen der Chemie, 1991, # 9, p. 875 - 878
  • 10
  • [ 13091-23-1 ]
  • [ 1681-37-4 ]
  • [ 40497-64-1 ]
  • [ 24484-96-6 ]
Reference: [1] Liebigs Annalen der Chemie, 1991, # 9, p. 875 - 878
  • 11
  • [ 13091-23-1 ]
  • [ 24843-31-0 ]
  • [ 5435-54-1 ]
Reference: [1] Patent: US4266060, 1981, A,
  • 12
  • [ 108-96-3 ]
  • [ 13091-23-1 ]
  • [ 5435-54-1 ]
Reference: [1] Journal of the Chemical Society, 1955, p. 2755,2761
  • 13
  • [ 15014-25-2 ]
  • [ 13091-23-1 ]
  • [ 5832-44-0 ]
  • [ 5435-54-1 ]
Reference: [1] Synthetic Communications, 1981, vol. 11, # 9, p. 743 - 750
  • 14
  • [ 5435-54-1 ]
  • [ 13091-23-1 ]
YieldReaction ConditionsOperation in experiment
99% With trichlorophosphate In toluene at 0 - 110℃; for 16 h; Heating / reflux Example 1 N-(3- { [2- (4-amino-furazan-3-yl)-1-phenyl-lH-imidazo [4, 5-c] pyridin-6- yl] oxy} phenyl) acetamide Step 1. 4-Chloro-3-nitropyridine To a suspension of 3-nitro-4-pyridinol (20 g, 143 mmol) in toluene (300 mL) was added phosphorous oxychloride (65.7g, 429mmol) at 0 °C. The resulting mixture was warmed to room temperature, then heated to reflux (110 °C) for 16 hours. After cooling to rt, the solvent was removed in vacuo and the residue was poured on ice, then basified with K2CO3 to pH = 10. The mixture was extracted with ethyl acetate and the organic phase was washed twice with water, followed by once with brine before concentrating to a brown oil which solidified on standing (22. 5g, 99percent). MS (ES+) m/e 159 [M+H] +.
99% With trichlorophosphate In toluene at 0 - 110℃; for 16 h; Heating / reflux Step 1. 4-Chloro-3-nitropyridine To a suspension of 3-nitro-4-pyridinol (20g, 143mmol) in toluene (300ml) was added phosphorous oxychloride (65.7g, 429mmol) at 0 °C. The resulting mixture was warmed to room temperature, then heated to reflux (110 °C) for 16 hours. After cooling to rt, the solvent was removed in vacuo and the residue was poured on ice, then basified by K2CO3 to pH = 10. The mixture was extracted with ethyl acetate and the organic phase was washed twice with water, followed by once with brine before concentrating to a brown oil which solidified on standing (22. 5g, 99percent)
99% With phosphorus pentachloride In trichlorophosphate for 3 h; Heating / reflux To a solution of 4-hydroxy-3-nitro-pyridine (2 g, 14 mmol) in POC13 (6 mL) was added PC15 (2.5 g, 12 mmol). The mixture was heated to reflux for 3 hours. The solvent was evaporated and the residue was cooled with ice-water and vigorously stirred with water (3 mL) and CHC13 (6 mL). The aqueous was extracted CHC13 (5x5 mL). The organic phase was combined and dried over MgSO4. After filtration, the solvent was removed to afford the product 4-Chloro-3-nitro-pyridine (2.24g, 99percent). 1H NMR (CDC13, 400 Hz) 8 9.13 (s, 1H), 8. 70 (d, J=5.2Hz, 1H), 7.55 (d, J=5.6Hz, 1H). MS (ESI+) [M+H] + 159.
99% With trichlorophosphate In toluene at 0 - 110℃; for 16 h; Heating / reflux Example 1 N-(3- { [2- (4-amino-furazan-3-yl)-1-phenyl-lH-imidazo [4, 5-c] pyridin-6- yl] oxy} phenyl) acetamide Step 1. 4-Chloro-3-nitropyridine To a suspension of 3-nitro-4-pyridinol (20 g, 143 mmol) in toluene (300 mL) was added phosphorous oxychloride (65.7g, 429mmol) at 0 °C. The resulting mixture was warmed to room temperature, then heated to reflux (110 °C) for 16 hours. After cooling to rt, the solvent was removed in vacuo and the residue was poured on ice, then basified with K2CO3 to pH = 10. The mixture was extracted with ethyl acetate and the organic phase was washed twice with water, followed by once with brine before concentrating to a brown oil which solidified on standing (22. 5g, 99percent). MS (ES+) m/e 159 [M+H] +.
99% With trichlorophosphate In toluene at 0 - 110℃; for 16 h; Heating / reflux Step 1. 4-Chloro-3-nitropyridine To a suspension of 3-nitro-4-pyridinol (20g, 143mmol) in toluene (300ml) was added phosphorous oxychloride (65.7g, 429mmol) at 0 °C. The resulting mixture was warmed to room temperature, then heated to reflux (110 °C) for 16 hours. After cooling to rt, the solvent was removed in vacuo and the residue was poured on ice, then basified by K2CO3 to pH = 10. The mixture was extracted with ethyl acetate and the organic phase was washed twice with water, followed by once with brine before concentrating to a brown oil which solidified on standing (22. 5g, 99percent)
97.8% With ammonium hydroxide; trichlorophosphate In water a)
4-Chloro-3-nitropyridine
Phosphorus oxychloride (25 ml, 0.27 mol) was added to 4-hydroxy-3-nitropyridine (7.0 g, 50.0 mmol), followed by reaction at 80° to 90° C. for 1.5 hours.
Phosphorus oxychloride was removed by distillation.
About 100 g of ice was added to the residue, and 28percent aqueous ammonia was added dropwise thereto to adjust the pH to 7.
Then, 100 ml of water was added thereto, and the aqueous mixture was extracted three times with 200 ml of dichloromethane.
The resulting dichloromethane layer was dried, and then dichloromethane was removed by distillation under reduced pressure to obtain 7.75 g of a yellow liquid (yield: 97.8percent).
97.8% With ammonium hydroxide; trichlorophosphate In water (a)
4-Chloro-3-nitropyridine
Phosphorus oxychloride (25 ml, 0.27 mol) was added to 4-hydroxy-3-nitropyridine (7.0 g, 50.0 mmol), followed by reaction at 80° to 90° C. for 1.5 hours.
Phosphorus oxychloride was removed by distillation.
About 100 g of ice was added to the residue, and 28percent aqueous ammonia was added dropwise thereto to adjust the pH to 7.
Then, 100 ml of water was added thereto, and the aqueous mixture was extracted three times with 200 ml of dichloromethane.
The resulting dichloromethane layer was dried, and then dichloromethane was removed by distillation under reduced pressure to obtain 7.75 g of a yellow liquid (yield: 97.8percent).
92% for 1 h; Heating / reflux 4-Hydroxy-3-nitropyridine ( 10.0 g, 71.38 mmol) was added to 100 ml of phosphorus oxychloride, which was then refluxed under stirring for 1 hour. The reaction mixture was concentrated under reduced pressure. The resulting residue was added to 500 ml of ice water, which was then neutralized with 2N sodium hydroxide solution. The reaction mixture was extracted with methylene chloride (300 ml). The separated organic layer was dried on anhydrous magnesium sulfate and concentrated under reduced pressure to give the titled compound of a pale yellow solid (9.2 g, 92.0percent).[50] TLC: n-hexane/ethyl acetate=2/l(v/v): Rf=O.5[51] * H-NMR (CDCl ) δ 9.12(s, IH), 8.69(d, IH), 7.55(d, IH)
92%
Stage #1: for 1 h; Heating / reflux
Stage #2: With sodium hydroxide In water at 0℃;
4-Hydroxy-3-nitropyridine (10 g, 71.38 mmol) was added to 100 ml of phosphorus oxychloride. The reaction mixture was refluxed for 1 hour and then concentrated under reduced pressure. The resulting residue was added to 500 ml of ice water and then neutralized with 2N sodium hydroxide solution. The reaction mixture was extracted with 300 ml of methylene chloride. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure to give the titled compound (9.2 g, 92.0 percent) as a pale yellow solid.[145] Rf (n-hexane/ethyl acetate = 2/1 , v/v) = 0.5[146] 1H-NMR (400MHz, CDCl ) δ 9.12(s,lH), 8.69(d,lH), 7.55(d,lH)
89% at 60 - 140℃; for 3.75 h; Example 4 2-{1-[4-(2-methoxy-5-nitropyridin-4-ylamino)phenyl]azetidin-3-yloxy}ethanol (4a) 4-chloro-3-nitropyridine To phosphorus pentachloride (16.3 g, 78.6 mmol) was added phosphorus oxychloride (16.2 mL, 173 mmol), 3-nitropyridin-4-ol (10.0 g, 71.4 mmol) was separately added at 60° C. over 15 min, and the mixture was stirred at 140° C. for 3.5 hr. The solvent was evaporated under reduced pressure, and the residue was poured into ice water, and neutralized with potassium carbonate. The mixture was extracted twice with chloroform, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate, 1:1, V/V). The solvent of the object fraction was evaporated under reduced pressure to give the title object compound as a pale-yellow powder (10.1 g, yield 89percent). 1H-NMR (CDCl3, 400 MHz) δ: 7.54 (1H, d, J=5.4 Hz), 8.69 (1H, d, J=5.4 Hz), 9.12 (1H, s).
77% at 70 - 140℃; for 5 h; Example 37 7- (2, 4-DICHLORO-PHENYL)-2-METHYL-2H-PYRAZOLO [4, 3-B] pyridine H N - NOZ O Cl Ar 103 104 =3w Br H2 NHZ NAcz X Ar Ar Ar 107 108 ste 110 N,-, 1 NHR Ar Ar Ar 111 113 Ar = 4-dichlorophenyl step 1 A mixture OF POC13 (22 mL) and PC15 (15 g) was warmed to 70° C and 4-hydroxy-3- nitropyridine (103,10 g) was added in small portions. A white solid formed and evolution of gas occurred. After the addition was completed the reaction was warmed to 140° C and the reaction stirred for 5 h. The reaction mixture was cooled and concentrated in vacuo. To the residue was added carefully H20 (50 ML) and the pH adjusted to 7.5 with solid NA2CO3. DCM was added and the two-phase mixture stirred for 30 min. The phases were separated and the aqueous phase washed twice with DCM (50 mL). The combined organic phases were dried (MgS04), filtered and evaporated to afford 104 (8.72 g, 77percent theory) which was sufficiently pure to use in the next step.
75% With trichlorophosphate In toluene at 0 - 110℃; for 14 h; To a suspension of 3-nitropyridin-4-ol (4.342 g, 31 mmol) in toluene (60 mL) was added POCl3 (11.6 mL, 124.4 mmol) at 0° C. The resulting mixture was warmed to room temperature, then heated to 110° C. for 14 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue was poured into ice, and basified with saturated aqueous NH4Cl solution. The mixture was extracted with EtOAc (40 mL.x.2). The combined organic layers was washed with water, brine, dried (MgSO4) and concentrated to a brown oil, which solidified on standing. (3.68 g, 75percent yield).1H NMR (DMSO-d6): δ ppm 9.23 (s, 1H), 8.80 (d, J=5.4 Hz, 1H), 7.91 (d, J=5.4 Hz, 1H).
67% With N,N-dimethyl-formamide; trichlorophosphate In toluene for 2 h; Inert atmosphere; Reflux 3-Nitropyridin-4-ol (334.4g, 2.37mol, 1.0wt) was charged to a 20000mL flask under nitrogen followed by toluene (5000mL, 15vol). Phosphorous oxychloride (1800mL, 5.4vol) was added slowly. N, N'-Dimethylformamide (1.73g, 0.024mol, 1molpercent) was added and the mixture heated at reflux for 2 hours. 1H-NMR indicated complete consumption of the starting material and the reaction was concentrated to dryness at 60oC and the residue azeotropically dried with toluene (4000mL, 12vol). Water (1600mL, 5vol) and tert butyl methyl ether (3300mL, 10vol) were added to the residue, the resulting mixture cooled in an ice bath and basified by portionwise addition of sodium carbonate (427g, 1.3wt). The mixture was transferred to a separating funnel, the layers separated and the aqueous layer extracted with tert butyl methyl ether (2x 3300mL, 2x 10vol). The combined organic fractions were washed with saturated brine (2000mL, 6vol), dried over magnesium sulphate, (334g, 1wt), filtered and concentrated to give the title compound 30 (253g, 67percent) as a brown oil.1H NMR (400MHz, DMSO): d 8.21 (d, J=5Hz, 1H), 9.03 (d, J=5Hz, 1H), 9.41 (s, 1H).
45% at 55 - 140℃; for 4 h; 4-Hydroxy-3-nitropyridine (10.0 g, 71.4 mmol) is added portionwise to a mechanically stirred mixture of phosphorous pentachloride (16.32 g, 78.6 mmol) and phosphorous oxychloride (16.2 mL) at 55-60° C. After the addition is complete, the temperature is raised to 130-140° C. for 4 hr. After cooling to room temperature, the phosphorous oxychloride is removed and the residue is cautiously treated with ice/water, made basic with sodium carbonate and extracted with ether. The combined extract is dried, filtered and concentrated to yield 4-chloro-3-nitropyridine (5.1 g, 45percent yield) as a pale yellow solid.

Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 1, p. 2 - 5
[2] Patent: WO2005/37197, 2005, A2, . Location in patent: Page/Page column 80; 83
[3] Patent: WO2005/37198, 2005, A2, . Location in patent: Page/Page column 20
[4] Patent: WO2005/51304, 2005, A2, . Location in patent: Page/Page column 70
[5] Patent: WO2005/51304, 2005, A2, . Location in patent: Page/Page column 70
[6] Patent: WO2005/37197, 2005, A2, . Location in patent: Page/Page column 80; 83
[7] Patent: WO2005/37198, 2005, A2, . Location in patent: Page/Page column 20
[8] Patent: US5262415, 1993, A,
[9] Patent: US5371086, 1994, A,
[10] Chemistry of Heterocyclic Compounds, 2012, vol. 48, # 8, p. 1235 - 1250[11] Khim. Geterotsikl. Soedin., 2012, vol. 48, # 8, p. 1235 - 1250,16
[12] Journal of Medicinal Chemistry, 1985, vol. 28, # 4, p. 467 - 471
[13] Patent: WO2006/38773, 2006, A1, . Location in patent: Page/Page column 7
[14] Patent: WO2007/1139, 2007, A1, . Location in patent: Page/Page column 11
[15] Journal of Materials Chemistry C, 2014, vol. 2, # 48, p. 10343 - 10356
[16] Patent: US2016/207883, 2016, A1, . Location in patent: Paragraph 0330-0332
[17] Journal of Medicinal Chemistry, 1989, vol. 32, # 11, p. 2474 - 2485
[18] Journal of Medicinal Chemistry, 2008, vol. 51, # 1, p. 17 - 30
[19] Patent: WO2005/16892, 2005, A1, . Location in patent: Page/Page column 106
[20] Patent: US2007/244164, 2007, A1, . Location in patent: Page/Page column 54
[21] Heterocycles, 1999, vol. 51, # 4, p. 721 - 726
[22] Tetrahedron Letters, 2010, vol. 51, # 26, p. 3353 - 3355
[23] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5292 - 5296
[24] Patent: US2005/54631, 2005, A1, . Location in patent: Page/Page column 24
[25] Pharmaceutica acta Helvetiae, 1975, vol. 50, # 6, p. 188 - 191
[26] Journal of the Chemical Society, 1955, p. 2755,2761
[27] Tetrahedron, 1981, vol. 37, p. 167 - 171
[28] Farmaco, Edizione Scientifica, 1983, vol. 38, # 5, p. 330 - 339
[29] Journal of Medicinal Chemistry, 1996, vol. 39, # 2, p. 487 - 493
[30] Tetrahedron, 2006, vol. 62, # 48, p. 11054 - 11062
[31] Journal of Medicinal Chemistry, 2001, vol. 44, # 3, p. 350 - 361
[32] Patent: US2006/47126, 2006, A1, . Location in patent: Page/Page column 24
[33] Patent: US5936089, 1999, A,
[34] Patent: US2004/63744, 2004, A1, . Location in patent: Page/Page column 46
[35] Patent: WO2011/5759, 2011, A2, . Location in patent: Page/Page column 68
[36] Patent: WO2014/120995, 2014, A2, . Location in patent: Page/Page column 189
[37] Patent: CN105622495, 2016, A, . Location in patent: Paragraph 0019; 0022
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  • 15
  • [ 626-64-2 ]
  • [ 13091-23-1 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 48, p. 11054 - 11062
[2] Journal of Medicinal Chemistry, 1989, vol. 32, # 11, p. 2474 - 2485
[3] Patent: US5550118, 1996, A,
[4] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5292 - 5296
[5] Chemistry of Heterocyclic Compounds, 2012, vol. 48, # 8, p. 1235 - 1250[6] Khim. Geterotsikl. Soedin., 2012, vol. 48, # 8, p. 1235 - 1250,16
[7] Journal of Materials Chemistry C, 2014, vol. 2, # 48, p. 10343 - 10356
  • 16
  • [ 5435-54-1 ]
  • [ 10025-87-3 ]
  • [ 13091-23-1 ]
Reference: [1] Patent: US6218539, 2001, B1,
  • 17
  • [ 15590-90-6 ]
  • [ 13091-23-1 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 50, p. 8607 - 8610
  • 18
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  • [ 13091-23-1 ]
Reference: [1] Patent: US6583138, 2003, B1,
  • 19
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  • [ 13091-23-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1985, vol. 28, # 4, p. 467 - 471
  • 20
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  • [ 13091-23-1 ]
Reference: [1] Roczniki Chemii, 1969, vol. 43, p. 923,932
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  • [ 13091-23-1 ]
Reference: [1] Journal of the Chemical Society, 1955, p. 2755,2761
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  • [ 13091-23-1 ]
Reference: [1] Chemische Berichte, 1927, vol. 60, p. 2108
  • 23
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  • [ 74-89-5 ]
  • [ 1633-41-6 ]
YieldReaction ConditionsOperation in experiment
98% at 40℃; for 1 h; To a suspension of 4-chloro-3-nitropyridine (2 g, 12.6 mmol) in dichloromethane (15 mL) was cautiously added methyl amine (25percent solution in water, 10 mL, 63 mmol). The reaction mixture was heated to 40° C. After stirring for 1 h, the mixture was poured into water (20 mL), and the precipitate was collected by filtration and dried in vacuo to afford the title compound (1.9 g, yield 98percent) as a yellow solid. LC-MS (ESI) m/z: 154 (M+1)+
98% at 40℃; for 1 h; Example 121 AN-Methyl-3 -nitropyridin-4-amine[00745] To a suspension of 4-chloro-3-nitropyridine (2 g, 12.6 mmol) in dichloromethane (15 mL) was cautiously added methyl amine (25percent solution in water, 10 mL, 63 mmol). The reaction mixture was heated to 40 °C. After stirring for 1 h, the mixture was poured into water (20 mL), and the precipitate was collected by filtration and dried in vacuo to afford the title compound (1.9 g, yield 98percent) as a yellow solid. LC-MS (ESI) m/z: 154 (M+l)+.
91% at 40℃; for 1 h; I. METHYL- (3-NITRO-PYRIDIN-4-YL)-AMINE To a suspension of 21.9 G (0.14 mol) 4-chloro-3-nitro-pyridine in 100 ml dichloromethane were cautiously added 62 ml (0.71 mol) methyl amine (40percent-SOLUTION in water) and the reaction was heated to 40 C. After stirring for 1H, the reaction mixture was poured into water (100 ML), the precipitate collected by filtration and dried in vacuo to afford 20 G (91 percent) of the title compound as a yellow solid. m. p. 159-162 C.
57.4% at 0 - 20℃; 4-Ch.oro-3-nitropyridine (70.0 g, 0.44 mol) was suspended in chloroform (280 mL) under stirring for 15 min. The suspension was cooled in an ice bath and diluted with ethanol (280 mL). Aqueous 40percent w/w solution of methylamine (98.2 mL) was added dropwise to this mixture under vigorous stirring and cooling. The reaction mixture was stirred at room temperature for 2 h and allowed to stay overnight. The mixture was diluted with chloroform (200 mL). The yellow precipitate was separated and washed with hot chloroform (400 mL). The filtrate was concentrated under reduced pressure to dryness, and the residue was dissolved in chloroform (800 mL). The solution was washed with water (2 * 800 mL) and dried over Na2SO4. The solvent was removed under reduced pressure, and the solid residue was recrystalfeed from acetone (750 mL) to give compound A/-Methyl-3-nitropyridin-4-amine (38.8 g, 57.4percent, 0.25 mol) as a yellow crystalline solid.
8.1% at -5 - 20℃; for 0.5 h; [0536] To a solution of compound 1 (200 g, 1.26 mol) in DCM (300 mL) was CH3NH2 (260 g, 2.5 mol) at -5°C to 30°C. After addition, the mixture was stuffed for 30 mins at rt. TLC showed the reaction was completed. The appeared solid was collected by filtration, the solid was washed with DCM to give one of the part crude compound 2 (178.3 g, 91.9 percent) as a yellow solid. The filtrate was concentrated and the residue was washed with DCM (50 mL) to give another part of the crude compound 2 (14.7 g, 8.1 percent) as a yellow solid.

Reference: [1] Patent: US2010/35883, 2010, A1, . Location in patent: Page/Page column 89
[2] Patent: WO2011/130661, 2011, A1, . Location in patent: Page/Page column 173
[3] Patent: WO2005/26164, 2005, A1, . Location in patent: Page/Page column 42
[4] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 563 - 566
[5] Patent: WO2008/12622, 2008, A2, . Location in patent: Page/Page column 55
[6] Patent: WO2015/153683, 2015, A1, . Location in patent: Paragraph 0536
[7] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 5023 - 5026
[8] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5493 - 5496
  • 24
  • [ 13091-23-1 ]
  • [ 1633-41-6 ]
Reference: [1] Patent: US5262415, 1993, A,
[2] Patent: US5371086, 1994, A,
  • 25
  • [ 13091-23-1 ]
  • [ 98-80-6 ]
  • [ 132038-21-2 ]
  • [ 31872-62-5 ]
Reference: [1] Heterocycles, 1999, vol. 51, # 4, p. 721 - 726
  • 26
  • [ 110-71-4 ]
  • [ 13091-23-1 ]
  • [ 132038-21-2 ]
  • [ 31872-62-5 ]
Reference: [1] Heterocycles, 1999, vol. 51, # 4, p. 721 - 726
  • 27
  • [ 67-56-1 ]
  • [ 13091-23-1 ]
  • [ 31872-62-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1937, vol. 529, p. 291
[2] Chemische Berichte, 1938, vol. 71, p. 2347,2358
[3] Chemische Berichte, 1942, vol. 75, p. 1936,1942
[4] Organic Letters, 2000, vol. 2, # 15, p. 2253 - 2256
  • 28
  • [ 124-41-4 ]
  • [ 13091-23-1 ]
  • [ 31872-62-5 ]
Reference: [1] Med.Ch.I.G., 1934, vol. 2, p. 384,387
  • 29
  • [ 13091-23-1 ]
  • [ 562825-95-0 ]
Reference: [1] Patent: US2003/212111, 2003, A1,
  • 30
  • [ 13091-23-1 ]
  • [ 1681-37-4 ]
  • [ 6980-08-1 ]
  • [ 40497-64-1 ]
  • [ 24484-96-6 ]
Reference: [1] Liebigs Annalen der Chemie, 1991, # 9, p. 875 - 878
  • 31
  • [ 13091-23-1 ]
  • [ 7205-46-1 ]
Reference: [1] Patent: EP2818472, 2014, A1,
  • 32
  • [ 13091-23-1 ]
  • [ 4487-56-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 1, p. 2 - 5
[2] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 2, p. 404 - 410
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 17, p. 7057 - 7075
[4] Patent: WO2015/115673, 2015, A1,
[5] Patent: EP2818472, 2014, A1,
[6] Patent: WO2005/37197, 2005, A2,
  • 33
  • [ 13091-23-1 ]
  • [ 4487-57-4 ]
Reference: [1] Patent: WO2014/81718, 2014, A1,
  • 34
  • [ 13091-23-1 ]
  • [ 24484-96-6 ]
YieldReaction ConditionsOperation in experiment
33% at -33 - 20℃; for 5 h; To 4-chloro-3-nitropyridine (10.0 g, 63.1 mmol) in 500 ml of liquid ammonium was added potassium permanganate (19.9 g, 126.1 mmol). The reaction was stirred at this temperature (-33 0C) for 5 hours then slowly warmed to room temperature. After evaporation of ammonia, water (1 L) was added. The solid formed was collected by filtration and washed with water (2 L). The solid was extracted with 1 : l=DCM:EtOAc (5x500 ml). The solvent was removed and the resulting solid was recrystallized from EtOAc (400 ml) to give the title compound as a yellow solid (4.4 g, 33percent). 1HNMR (400 MHz) 8.88 (s, IH), 7.65 (b, 2H), 6.62 (s, IH).
Reference: [1] Patent: WO2006/87530, 2006, A1, . Location in patent: Page/Page column 73
  • 35
  • [ 13091-23-1 ]
  • [ 1681-37-4 ]
  • [ 6980-08-1 ]
  • [ 40497-64-1 ]
  • [ 24484-96-6 ]
Reference: [1] Liebigs Annalen der Chemie, 1991, # 9, p. 875 - 878
  • 36
  • [ 13091-23-1 ]
  • [ 1681-37-4 ]
  • [ 40497-64-1 ]
  • [ 24484-96-6 ]
Reference: [1] Liebigs Annalen der Chemie, 1991, # 9, p. 875 - 878
  • 37
  • [ 13091-23-1 ]
  • [ 146140-99-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 1, p. 304 - 309[2] Angew. Chem., 2013, vol. 125, # 1, p. 322 - 327,6
[3] Patent: WO2018/98411, 2018, A1,
  • 38
  • [ 1826-67-1 ]
  • [ 13091-23-1 ]
  • [ 357263-48-0 ]
YieldReaction ConditionsOperation in experiment
16%
Stage #1: at -78 - -20℃; for 8 h;
Stage #2: With ammonium chloride In tetrahydrofuran; water
To a solution of 4-chloro-3-nitro-pyridine (2 g, 13 mmol) in dry THF (100 mL) under N2 at-78°C was added excess vinyl magnesium bromide (1. OM, 40 mL, 40 mmol). The mixture was stirred at-20 °C for 8 hours before the reaction was quenched with 20percent NH4C1 (75 mL). The aqueous phase was extracted with ethyl acetate (3x100 mL). The combined organic layer was dried over MgS04, filtered and concentrated. The residue was subject to chromatography on silica gel to afford 7-Chloro-lH-pyrrolo [3,2-b] pyridine (0.3g, 16percent). IH NMR (CD30D, 400 Hz) 8 8.22 (d, J=5.2Hz, 1H), 7.64 (d, J=3. 2Hz, 1H), 7. 23 (d, J=5.2Hz, 1H), 6.67 (d, J=3.2Hz, 1H). MS (ESI+) [M+H] + 153.
11%
Stage #1: at -78 - -20℃; for 8 h;
Stage #2: With water; ammonium chloride In tetrahydrofuran
To a solution of 2-chloro-3-nitropyridine (2.0g, 12.6mmol) [C. Almansa. et al.,J. Med. Chem.. 2001. 44. 350-3611 in THF (80mL) at -78°C, was added vinylmagnesiumbromide (80mL, 1 .OM in THF), and the reaction mixture was stirred at -20°C for 8 hours,quenched with NHjCl solution (20percent, lOOmL), extracted with EtOAc, dried over anhydrousNa2SC>4 and concentrated. The residue was purified by flash column chromatography, eluentEtOAc/Hexane (1:1), to afford the title compound 266 (240mg, 11percent) as yellow crystals.MS (m/z): 153.1(M+H) (found).
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 7, p. 2345 - 2347
[2] Patent: WO2005/51304, 2005, A2, . Location in patent: Page/Page column 70
[3] Patent: WO2005/51304, 2005, A2, . Location in patent: Page/Page column 70
[4] Patent: WO2006/10264, 2006, A1, . Location in patent: Page/Page column 203
[5] Patent: US2004/63744, 2004, A1, . Location in patent: Page/Page column 46
[6] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 213 - 217
  • 39
  • [ 13091-23-1 ]
  • [ 357263-48-0 ]
Reference: [1] Patent: US2005/261296, 2005, A1,
  • 40
  • [ 13091-23-1 ]
  • [ 850663-54-6 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With tert.-butylhydroperoxide; potassium <i>tert</i>-butylate; ammonia In tetrahydrofuran; decane at -78 - 0℃; for 1.5 h;
Stage #2: With ammonium chloride In tetrahydrofuran; decane; water at -35 - 20℃;
Ammonia (74.0 mL, 3418.64 mmol) was condensed into THF (170 mL) cooled to -78 0C under nitrogen. Potassium tert-butoxide (23.98 g, 213.67 mmol) was added as a solid and the reaction mixture warmed to -35 0C. tert-Butyl hydroperoxide (5.5 M soln. in decane) (16.32 mL, 89.74 mmol) was added dropwise to 4-chloro-3-nitropyridine (13.55 g, 85.47 mmol) in THF (200 mL) cooled to 0 0C over a period of 5 minutes under nitrogen. The <n="158"/>resulting solution was added slowly to the other flask and the mixture stirred at -35 0C for 1.5 hours. The reaction mixture was quenched with saturated NH4CI (50 mL) and allowed to warm to room temperature overnight. The reaction mixture was concentrated in vacuo and the brown precipitate filtered and washed with cold water to yield crude product. The solid was dried overnight under vacuum to yield 4-chloro-5-nitropyridin-2-ol (14.66 g, 83.99 mmol, 98 percent) as a yellow solid. 1R NMR (400 MHz, DMSO) δ 6.36 (IH, s), 8.73 (IH, s). m/z 173 (M-H)".
95% With tert.-butylhydroperoxide; potassium <i>tert</i>-butylate; ammonia In tetrahydrofuran; decane at -40 - 0℃; for 2.75 h; Inert atmosphere 11.7
Synthesis of 2,4-dichloro-5-nitro-pyridin-2-ol 12*
Ammonia (∼80 mL) was condensed into a stirred -78 °C solution of THF (250 mL) under a nitrogen atmosphere.
Potassium tert-butoxide (35.5 g, 316 mmol) was added to the mixture before allowing it to warm to -40 °C. Separately, a suspension of 4-chloro-3-nitropyridine (20 g, 126.2 mmol) in THF (100 mL) was cooled to 0 °C and a solution of tert-butyl hydroperoxide (6 M in decane, 21 mL, 126 mmol) was added over 10 minutes.
The suspension was stirred for a further 5 minutes before adding the solution drop-wise to the ammonia mixture over 1 h.
The reaction mixture was stirred for a further 1.5 h between -35 °C and -40 °C, before carefully quenching with saturated NH4Cl solution (25 mL).
The reaction mixture was allowed to stir and vent overnight before the solvents were removed under vacuum with very careful vacuum regulation (∼600 mbar initially).
The crude solid was purified by trituration with ice cold saturated NH4Cl solution (50 mL), filtering onto a sinter.
The solid was washed with ice cold water (2 x 25 mL) before drying under vacuum to give the intermediate phenol compound as a yellow solid (20.9 g, 95percent).
1H NMR (400 MHz, DMSO) δ(ppm): 8.8 (1 H, s), 7.0 (1 H, s), 5.9 (1 H, s). LC-MS: Rt=1.7 min, [M-H]- 175; [M+H]+ 177.
90% With tert.-butylhydroperoxide; potassium <i>tert</i>-butylate; ammonia In tetrahydrofuran for 5 h; Cooling with ice Ammonia gas (100 mL) was condensed into THF (300 mL) at -78°C in a cardice/acetone bath. Potassium tert- butoxide (395 mmol, 44.25 g) was then added portion-wise with stirring. After 5 minutes, the cardice bath was lowered so only the bottom quarter of the flask was immersed and stirring was continued for a further 20 minutes. Concurrently, tert-butyl hydroperoxide (158 mmol, 26.3 mL) was added to a suspension of 4-chloro-3- nitropyridine (158 mmol, 25 g) in THF (100 mL) cooled in an ice/water bath. This mixture was stirred for 45 minutes then transferred to a dropping funnel and added drop-wise over 1.25 hours to the ammonia solution (0797) prepared above. The mixture was stirred for a further 3 hours then saturated aqueous ammonium chloride solution (35 mL) was added carefully. The mixture was allowed to warm to room temperature overnight allowing the ammonia to vent to atmosphere. The solvents were then removed under reduced pressure and the residue triturated with ice-cold saturated aqueous ammonium chloride solution (50 mL) . The resulting solid was collected by filtration, washed with ice-cold water (2 x 50 mL) then dried under suction prior to further drying by azeotroping with toluene (5 x 100 mL) then in a vacuum oven at 40°C overnight to give the title compound as a brown solid (24.96 g, 90percent) .
80% With tert.-butylhydroperoxide; potassium <i>tert</i>-butylate; ammonia In tetrahydrofuran; decane at -78 - 0℃; for 3.08333 h; Step 2. 4-Chloro-2-hydroxy-5-nitropyridine THF (500 mL) was cooled to-78 °C and anhydrous NH3 (-200 mL) was condensed into the THF. Potassium t-butoxid (71.0 g, 630 mmol) was added and the mixture was allowed to warm to--35 OC. The product from Step 1 (40.0 g, 250 mmol) was cooled to 0 °C in THF (200 mL) and a solution of t-BuOOH (5 M in decane, 50 mL, 250 mmol) was added over 5 min. This solution was then added dropwise to the KOt-Bu solution prepared above over 1 h, then stirred for 2 h at-35 °C and then carefully quenched with-50 mL of sat. NH4C1 solution. The mixture was allowed to vent and warm to rt overnight, then the organics were concentrated and the residue made acidic with NH4Cl solution and filtered. The solid was washed with cold H20 and dried to give the title compound as a dark brown solid (35 g, 80 percent).
80% With tert.-butylhydroperoxide; potassium <i>tert</i>-butylate; ammonia In tetrahydrofuran; decane at -78 - 0℃; for 3.08333 h; Step 2. 4-Chloro-2-hydroxy-5-nitropyridine THF (500 mL) was cooled to-78 °C and anhydrous NH3 (-200 mL) was condensed into the THF. Potassium t-butoxid (71.0 g, 630 mmol) was added and the mixture was allowed to warm to--35 OC. The product from Step 1 (40.0 g, 250 mmol) was cooled to 0 °C in THF (200 mL) and a solution of t-BuOOH (5 M in decane, 50 mL, 250 mmol) was added over 5 min. This solution was then added dropwise to the KOt-Bu solution prepared above over 1 h, then stirred for 2 h at-35 °C and then carefully quenched with-50 mL of sat. NH4C1 solution. The mixture was allowed to vent and warm to rt overnight, then the organics were concentrated and the residue made acidic with NH4Cl solution and filtered. The solid was washed with cold H20 and dried to give the title compound as a dark brown solid (35 g, 80 percent).
39% With tert.-butylhydroperoxide; potassium <i>tert</i>-butylate; ammonia In tetrahydrofuran at -70 - -40℃; for 2 h; Inert atmosphere Into a 1 L 4-necked round-bottom flask purged and maintained with nitrogen, was added tetrahydrofuran (200 mL). Ammonia gas was bubbled into the solution at -70 °C to afford a saturated solution of ammonia. To the mixture was added t-BuOK (53.1 g, 0.473 mol) at -70 °C, providing solution (I). Into another 5 L 4-necked round-bottom flask purged and maintained with nitrogen, was added a solution of 4-chloro-3-nitropyridine (30.0 g, 0.189 mol) in tetrahydrofuran (200 mL). To the mixture was added i-BuOOH (53.1 g, 0.473 mol) at 0 °C to afford a solution (II) Solution (II) was added dropwise into Solution (I) at -70 °C, the resulting solution was stirred at - 40 °C for 2 hours. The reaction mixture was quenched by addition of saturated aqueous ammonium chloride and concentrated under vacuum. The residue was triturated with water, and the solids were collected by filtration, washed with THF (50 mL) and dried under vacuum to afford 4-chloro-5-nitropyridin-2-ol (13.0 g, 39.0 percent) as a yellow solid. LCMS (ESI): RT (min) = 0.535, [M+H]+ = 175, method = G. 'HNMR (400 MHz, DMSO-d6) 8.80 (s, 1H), 6.98 (br, 1H), 5.91 (s, 1H).
34%
Stage #1: With tert.-butylhydroperoxide In tetrahydrofuran; decaneCooling with ice
Stage #2: With potassium <i>tert</i>-butylate; ammonia In tetrahydrofuran; decane at -35℃; for 2.5 h;
(4b) 4-chloro-5-nitropyridin-2-ol Ammonia gas was bubbled against tetrahydrofuran (60 mL) at −78° C. for 1.5 hr, potassium tert-butoxide (8.88 g, 78.8 mmol) was added, and the mixture was heated to −35° C. 4-Chloro-3-nitropyridine (5.00 g, 31.5 mmol) produced in Example 4 (4a) was dissolved in tetrahydrofuran (25 mL) and, under ice-cooling, 5.5 M tert-butylhydrogen peroxide/decane solution (31.0 mL, 171 mmol) was added. This solution was added dropwise to the ammonia solution prepared earlier over 1 hr, and the mixture was stirred at the same temperature for 1.5 hr. To the reaction mixture was added saturated ammonium chloride water to separate the mixture into two layers. The organic layer was evaporated under reduced pressure, saturated aqueous ammonium chloride was added and the precipitate was collected by filtration and washed with water to give the title object compound as a pale-brown powder (670 mg). The filtrate was extracted twice with ethyl acetate, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the precipitated powder was collected by filtration with hexane to give the title object compound as a pale-brown powder (1.18 g, total yield 34percent). 1H-NMR (CDCl3, 400 MHz) δ: 6.69 (1H, s), 8.71 (1H, s), 12.80-13.05 (1H, br).

Reference: [1] Patent: WO2009/24821, 2009, A2, . Location in patent: Page/Page column 156-157
[2] Patent: EP2818472, 2014, A1, . Location in patent: Paragraph 0126; 0127
[3] Tetrahedron Letters, 2010, vol. 51, # 21, p. 2800 - 2802
[4] Patent: WO2015/115673, 2015, A1, . Location in patent: Page/Page column 79-80
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 1, p. 2 - 5
[6] Patent: WO2005/37197, 2005, A2, . Location in patent: Page/Page column 80; 83
[7] Patent: WO2005/37197, 2005, A2, . Location in patent: Page/Page column 80; 83
[8] Journal of Medicinal Chemistry, 2015, vol. 58, # 17, p. 7057 - 7075
[9] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 2, p. 404 - 410
[10] Patent: WO2014/81718, 2014, A1, . Location in patent: Page/Page column 114
[11] Patent: US2016/207883, 2016, A1, . Location in patent: Paragraph 0333-0335
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