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[ CAS No. 4684-94-0 ] {[proInfo.proName]}

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Chemical Structure| 4684-94-0
Chemical Structure| 4684-94-0
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Product Details of [ 4684-94-0 ]

CAS No. :4684-94-0 MDL No. :MFCD00155390
Formula : C6H4ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZLKMOIHCHCMSFW-UHFFFAOYSA-N
M.W : 157.55 Pubchem ID :20812
Synonyms :

Calculated chemistry of [ 4684-94-0 ]

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 : 1.0
Molar Refractivity : 36.21
TPSA : 50.19 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) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.97
Log Po/w (XLOGP3) : 1.5
Log Po/w (WLOGP) : 1.43
Log Po/w (MLOGP) : -0.51
Log Po/w (SILICOS-IT) : 1.39
Consensus Log Po/w : 0.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.14
Solubility : 1.14 mg/ml ; 0.00725 mol/l
Class : Soluble
Log S (Ali) : -2.16
Solubility : 1.09 mg/ml ; 0.00689 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.0
Solubility : 1.57 mg/ml ; 0.00998 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.43

Safety of [ 4684-94-0 ]

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

Application In Synthesis of [ 4684-94-0 ]

* 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 [ 4684-94-0 ]
  • Downstream synthetic route of [ 4684-94-0 ]

[ 4684-94-0 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 4684-94-0 ]
  • [ 75-16-1 ]
  • [ 55676-22-7 ]
Reference: [1] Patent: US6034275, 2000, A,
  • 2
  • [ 4684-94-0 ]
  • [ 45644-21-1 ]
Reference: [1] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
  • 3
  • [ 4684-94-0 ]
  • [ 17920-35-3 ]
Reference: [1] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
  • 4
  • [ 4684-94-0 ]
  • [ 23628-31-1 ]
Reference: [1] Patent: CH227124, 1941, ,
  • 5
  • [ 1929-82-4 ]
  • [ 4684-94-0 ]
YieldReaction ConditionsOperation in experiment
90% at 100℃; for 8 h; 2-chloro-6-trichloromethylpyridine (115.5 g, 0.5 mol) and 98percent concentrated sulfuric acid (60 g, 0.6 mol) were sequentially added to a 500 mL three-necked flask equipped with a thermometer, and heated to 100 ° C for 8.0 h. . After the reaction was completed, the temperature was lowered to 60 ° C, 27percent aqueous ammonia was added dropwise and neutralized to pH = 7. After cooling to room temperature and stirring, a solid was precipitated and suction filtered to give a white solid, yield: 90percent, m.p.: 192 to 193
Reference: [1] Patent: CN108530351, 2018, A, . Location in patent: Paragraph 0011; 0026; 0027
  • 6
  • [ 2402-78-0 ]
  • [ 124-38-9 ]
  • [ 4684-94-0 ]
Reference: [1] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 82, p. 11574 - 11577
  • 7
  • [ 5140-72-7 ]
  • [ 124-38-9 ]
  • [ 4684-94-0 ]
Reference: [1] Archiv der Pharmazie, 2000, vol. 333, # 5, p. 107 - 112
  • 8
  • [ 5140-72-7 ]
  • [ 2258-42-6 ]
  • [ 4684-94-0 ]
Reference: [1] Synthetic Communications, 2012, vol. 42, # 5, p. 658 - 666
  • 9
  • [ 18368-63-3 ]
  • [ 4684-94-0 ]
Reference: [1] Angewandte Chemie, 1992, vol. 104, # 6, p. 748 - 749
[2] Angewandte Chemie, 1992, vol. 104, # 6, p. 748 - 749
[3] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[4] Journal of Organic Chemistry, 1958, vol. 23, p. 1287
[5] Patent: CH227124, 1941, ,
  • 10
  • [ 67-56-1 ]
  • [ 4684-94-0 ]
  • [ 6636-55-1 ]
YieldReaction ConditionsOperation in experiment
100% at 0 - 50℃; for 6.75 h; Add thionyl chloride (3.7 ml, 50.8 mmol) to a solution of 6-chloropicolinic acid (4.0 g, 25.4 mmol) in methanol (85 ml) at 0 C. Stir the resultant solution for 15 minutes at 0 C, 0.5 hours at room temperature, and 6 hours at 50 C. Concentrate the reaction in vacuo and dilute with CHCl3 (150ml). Wash the organic solution with saturated aqueous sodium bicarbonate (3 x 100 ml), and brine (1 x 100 ml) and dry with sodium sulfate. Filtration and concentration afford methyl 6-chloropicolinate 4.38 g (100 percent) as a white solid. 1H NMR (CDCl3): δ 8.05 (m, 1H), 7.73 (m, 1H), 7.42 (m, 1H), 3.95 (s, 3H)
95%
Stage #1: for 15 h; Heating / reflux
Stage #2: With sodium hydroxide In water
PREPARATION 1: Preparation of β-chloropyridine-^-carboxylic acid methyl ester6.5 g (41.2 mmol) of -chloropyridine^-carboxylic acid was dissolved in 100 ml of methanol, and 5 ml of 2 N hydrochloric acid solution in methanol was added thereto, then stirred under reflux for 15 hours. After completion of the reaction, the reaction solution was concentrated, and 100 ml of water was added thereto, then neutralized using 1 N aqueous sodium hydroxide solution. The resulting solution was extracted twice with 70 ml of ethyl acetate, and concentrated to obtanin 6.69 g (39.1 mmol, yield of 95percent) of the title compound.1H NMR (CDCl3, ppm); δ 7.71(1H, d), 7.33(1H, t), 7.14(1H, d), 3.65(3H, s)FAB MS(m/e) = 172 [M+l]
Reference: [1] Patent: WO2004/26871, 2004, A1, . Location in patent: Page 43
[2] Patent: WO2007/58482, 2007, A1, . Location in patent: Page/Page column 47
[3] Patent: WO2013/102431, 2013, A1, . Location in patent: Page/Page column 117
[4] Patent: WO2015/6592, 2015, A1, . Location in patent: Page/Page column 52; 53
  • 11
  • [ 4684-94-0 ]
  • [ 6636-55-1 ]
Reference: [1] Journal of Organic Chemistry, 1958, vol. 23, p. 1287
[2] Patent: WO2012/49277, 2012, A1,
[3] Patent: US2013/289020, 2013, A1,
  • 12
  • [ 4684-94-0 ]
  • [ 598-99-2 ]
  • [ 6636-55-1 ]
Reference: [1] Synthetic Communications, 1984, vol. 14, # 1, p. 77 - 82
  • 13
  • [ 4684-94-0 ]
  • [ 16045-88-8 ]
  • [ 6636-55-1 ]
Reference: [1] Journal of Pharmaceutical Sciences, 1989, vol. 78, # 3, p. 206 - 210
  • 14
  • [ 4684-94-0 ]
  • [ 80099-98-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 2, p. 125 - 128
[2] Archiv der Pharmazie, 2000, vol. 333, # 5, p. 107 - 112
[3] Patent: WO2008/729, 2008, A1, . Location in patent: Page/Page column 94
[4] Patent: WO2008/82487, 2008, A2, . Location in patent: Page/Page column 150
[5] Patent: US2009/162453, 2009, A1, . Location in patent: Page/Page column 95
[6] Patent: EP1207154, 2002, A1, . Location in patent: Example 21
[7] Patent: EP1661886, 2006, A1, . Location in patent: Page/Page column 148
[8] Patent: EP1714958, 2006, A1, . Location in patent: Page/Page column 164
[9] Patent: WO2012/49277, 2012, A1, . Location in patent: Page/Page column 37
[10] Patent: US2013/289020, 2013, A1, . Location in patent: Paragraph 0135; 0137; 0139
[11] Advanced Synthesis and Catalysis, 2014, vol. 356, # 5, p. 1038 - 1046
[12] Patent: EP2712862, 2014, A1, . Location in patent: Paragraph 0087
[13] Angewandte Chemie - International Edition, 2018, [14] Angew. Chem., 2018, vol. 130, p. 15988 - 15992,5
  • 15
  • [ 4684-94-0 ]
  • [ 73896-36-3 ]
Reference: [1] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
  • 16
  • [ 4684-94-0 ]
  • [ 64-17-5 ]
  • [ 21190-89-6 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With sulfuric acid In toluene for 3 h; Reflux
Stage #2: With potassium carbonate In water; ethyl acetate
Step D: Preparation of ethyl 6-chloropicolinate: A flask equipped with a condenser was charged with 6-chloropicolinic acid (23.5 g, 149 mmol), 100 mL of ethanol and 400 mL of toluene. To this was added 4 mL of sulfuric acid and the mixture was warmed to reflux for three hours, and then allowed to cool to ambient temperature. The reaction mixture was concentrated under reduced pressure and the resulting oil was taken up in 200 mL of ethyl acetate, washed with 10percent aqueous potassium carbonate, dried over sodium sulfate and concentrated under reduced pressure to give 26 g of ethyl 6-chloropicolinate (94percent).
Reference: [1] Patent: WO2012/82689, 2012, A1, . Location in patent: Page/Page column 56
[2] European Journal of Organic Chemistry, 2014, vol. 2014, # 28, p. 6295 - 6302
[3] Organic Letters, 2014, vol. 16, # 15, p. 3860 - 3863
  • 17
  • [ 4684-94-0 ]
  • [ 21190-89-6 ]
YieldReaction ConditionsOperation in experiment
91% With thionyl chloride; triethylamine In 1,4-dioxane; ethanol; water Example 8
6-(4-(3-(10,11-Dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-1-piperazinyl)-2-pyridinecarboxylic acid hydrochloride STR14
To a suspension of 6-chloropyridine-2-carboxylic acid (8.3 g, 0.0525 mol, prepared as described in Chem.Ber.45, 2456 (1912)) in dioxane (25 ml), thionyl chloride (9.4 ml, 0.13 mol) was added and the resulting mixture was stirred at 70° C. for 4 h.
The reaction mixture was concentrated in vacuo and a mixture of dioxane (8.3 ml) and ethanol (16.6 ml) was added.
The reaction mixture was heated to 70° C. for 2 h, triethylamine (8.3 ml), ethanol (4.1 ml) and water (8.3 ml) were added and the reaction mixture was again concentrated.
The residue was distributed between diethyl ether (28 ml) and water (18 ml) and the phases were separated.
The aqueous layer was extracted with diethyl ether (30 ml) and the combined organic layers were dried (MgSO4) and evaporated in vacuo.
This afforded 8.82 g (91percent) of 6-chloropyridine-2-carboxylic acid ethyl ester as an oil.
Reference: [1] Patent: US6649627, 2003, B1,
[2] Patent: US5916889, 1999, A,
  • 18
  • [ 4684-94-0 ]
  • [ 33674-97-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[2] Patent: WO2011/47156, 2011, A1, . Location in patent: Page/Page column 96
  • 19
  • [ 4684-94-0 ]
  • [ 33674-97-4 ]
Reference: [1] Patent: US2003/105106, 2003, A1,
  • 20
  • [ 4684-94-0 ]
  • [ 54087-03-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
  • 21
  • [ 4684-94-0 ]
  • [ 78846-88-5 ]
Reference: [1] Patent: WO2011/47156, 2011, A1,
  • 22
  • [ 4684-94-0 ]
  • [ 75-65-0 ]
  • [ 159603-71-1 ]
Reference: [1] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
  • 23
  • [ 4684-94-0 ]
  • [ 75279-60-6 ]
Reference: [1] Patent: WO2011/47156, 2011, A1,
  • 24
  • [ 4684-94-0 ]
  • [ 98-17-9 ]
  • [ 137640-84-7 ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate; copper(l) chloride In N,N-dimethyl-formamide at 140℃; for 6 h; To 500mL three-necked flask equipped with a thermometer, was added DMF (200ml), between sequentially added trifluoromethylphenol (0.26mol, 42.2g), potassium carbonate (0.266mol, 37.2g), 2-chloro-6-carboxy pyridine (0.2mol, 31.6g), cuprous chloride (1.0 g of), heated to 140 deg.] C, the reaction 6.0H, cooled to room temperature, the reaction solution was poured into 600ml of ice water, pH = 3 adjusted with concentrated brine, and the precipitated solid was pumped was filtered off, washed with water, dried to obtain a white solid, yield: 75percent
Reference: [1] Patent: CN108530351, 2018, A, . Location in patent: Paragraph 0011; 0026; 0028
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