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[ CAS No. 1189513-51-6 ] {[proInfo.proName]}

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Chemical Structure| 1189513-51-6
Chemical Structure| 1189513-51-6
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Product Details of [ 1189513-51-6 ]

CAS No. :1189513-51-6 MDL No. :MFCD12827552
Formula : C6H3BrClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KPHRXSNSIGEBSN-UHFFFAOYSA-N
M.W :236.45 Pubchem ID :45933815
Synonyms :

Calculated chemistry of [ 1189513-51-6 ]

Physicochemical Properties

Num. heavy atoms : 11
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 : 43.91
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) : -6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.34
Log Po/w (XLOGP3) : 2.03
Log Po/w (WLOGP) : 2.2
Log Po/w (MLOGP) : 0.25
Log Po/w (SILICOS-IT) : 2.08
Consensus Log Po/w : 1.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.92
Solubility : 0.283 mg/ml ; 0.0012 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.459 mg/ml ; 0.00194 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.87
Solubility : 0.316 mg/ml ; 0.00134 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 1189513-51-6 ]

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:

Application In Synthesis of [ 1189513-51-6 ]

* 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 [ 1189513-51-6 ]
  • Downstream synthetic route of [ 1189513-51-6 ]

[ 1189513-51-6 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 1189513-51-6 ]
  • [ 1206968-88-8 ]
Reference: [1] Patent: WO2015/89327, 2015, A1, . Location in patent: Paragraph 0223
  • 2
  • [ 1189513-51-6 ]
  • [ 885168-04-7 ]
Reference: [1] Patent: EP2862856, 2015, A1, . Location in patent: Paragraph 0960
[2] Patent: WO2015/158427, 2015, A1,
[3] Patent: WO2012/81736, 2012, A1,
  • 3
  • [ 67-56-1 ]
  • [ 1189513-51-6 ]
  • [ 1214336-41-0 ]
YieldReaction ConditionsOperation in experiment
55 g
Stage #1: With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3 h;
Stage #2: at 10 - 20℃;
To a slightly cloudy solution of 5-bromo-3-chloro-pyridine-2-carboxylic acid (60 g, 183.2 mmol) in dichloromethane (700 ml) was added dropwise N,N-dimethylformamide (1 ml) and oxalyl chloride (24,9 ml, 286.9 mmol). The cloudy solution was stirred for 3 hours at ambient temperature. Theresulting yellow solution was cooled to 10°C and methanol (30.8 ml, 761.3 mmol) was added dropwise to the mixture, keeping the temperature between 15° and 20°C. The solution was stirred overnight at ambient temperature. After neutralisation with an aqueous saturated solution of sodium hydrogen carbonate, the organic layer was washed with brine, dried over sodium sulfate, filtrated and evaporated to give methyl 5-bromo-3-chloro-pyridine-2-carboxylate (55 g) as a yellow solid, which was used without further purification. LCMS (method B): 250/252/254 (M+1), retention time 1.12 mm.
55 g
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3 h;
Stage #2: at 10 - 20℃;
To a slightly cloudy solution of 5-bromo-3-chloro-pyridine-2-carboxylic acid (60 g, 183.2 mmol) indichloromethane (700 ml) was added dropwise N,N-dimethylformamide (1 ml) and oxalylchloride (24,9ml, 286.9 mmol). The cloudy solution was stirred for 3 hours at ambient temperature. The resulting yellow solution was cooled to 10°C and methanol (30.8 ml, 761.3 mmol) was added dropwise to the mixture, keeping the temperature between 15° and 20°C. The solution was stirred overnight at ambient temperature. After neutralisation with an aqueous saturated solution of sodium hydrogencarbonate, the organic layer was washed with brine, dried over sodium sulfate, filtrated and evaporated to give methyl 5-bromo-3-chloro-pyridine-2-carboxylate (55 g) as a yellow solid, which was used without further purification. LCMS (method 2): 250/252/254 (M+1), retention time 1.12 mm.
55 g
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3 h;
Stage #2: at 10 - 20℃;
Step 1: Preparation of methyl 5-bromo-3-chloro-pyridine-2-carboxylate To a slightly cloudy solution of 5-bromo-3-chloro-pyridine-2-carboxylic acid (60 g, 183.2 mmol) in dichloromethane (700 ml) was added dropwise N,N-dimethylformamide (1 ml) and oxalylchloride (24,9 ml, 286.9 mmol). The cloudy solution was stirred for 3 hours at room temperature. The resulting yellow solution was cooled to 10°C and methanol (30.8 ml, 761.3 mmol) was added dropwise to the mixture, keeping the temperature between 15° and 20°C. The solution was stirred overnight at room temperature. After neutralisation with an aqueous saturated solution of sodium hydrogen carbonate, the organic layer was washed with brine, dried over sodium sulfate, filtrated and evaporated to give methyl 5-bromo-3-chloro-pyridine-2-carboxylate (55 g) as a yellow solid, which was used without further purification. LCMS (method 2): 250/252/254 (M+1)+ , retention time 1.12 min.
55 g
Stage #1: With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 10 - 20℃; for 3 h;
Stage #2: at 15 - 20℃;
To a slightly cloudy solution of 5-bromo-3-chloro-pyridine-2-carboxylic acid (60 g, 183.2 mmol) in dichloromethane (700 ml) was added dropwise N,N-dimethylformamide (1 ml) and oxalylchloride (24,9 ml, 286.9 mmol). The cloudy solution was stirred for 3 hours at ambient temperature. The resulting yellow solution was cooled to 10°C and methanol (30.8 ml, 761 .3 mmol) was added dropwise to the mixture, keeping the temperature between 15° and 20°C. The solution was stirred overnight at ambient temperature. After neutralization with an aqueous saturated solution of sodium hydrogen carbonate, the organic layer was washed with brine, dried over sodium sulfate, filtrated and evaporated to give methyl 5- bromo-3-chloro-pyridine-2-carboxylate (55 g) as a yellow solid, which was used without further purification. LCMS (method 2): 250/252/254 (M+1 )+, retention time 1 .12 min.

Reference: [1] Patent: WO2015/160636, 2015, A1, . Location in patent: Page/Page column 164
[2] Patent: WO2015/160634, 2015, A1, . Location in patent: Page/Page column 145
[3] Patent: WO2016/46071, 2016, A1, . Location in patent: Page/Page column 61
[4] Patent: WO2016/87265, 2016, A1, . Location in patent: Page/Page column 62; 63
[5] Patent: WO2016/87257, 2016, A1, . Location in patent: Page/Page column 67-68
[6] Patent: WO2016/120182, 2016, A1, . Location in patent: Page/Page column 49
  • 4
  • [ 1189513-51-6 ]
  • [ 1214336-41-0 ]
Reference: [1] Patent: WO2017/16910, 2017, A1,
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