Ethanol → HCID 67958121, compound

HRID 450345Notes

Reaction equation

HRID 450345 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[N:24]=[C:23]([NH:25][C:26]3[C:31]([Cl:32])=[CH:30][CH:29]=[C:28]([CH2:33][NH:34][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])[C:27]=3[Cl:41])[N:22]([CH3:42])[C:9]2=[N:10][C:11]=1[N:12]1[CH2:17][CH2:16][CH:15]([C:18]([F:21])([F:20])[F:19])[CH2:14][CH2:13]1)=[O:5])C.CCO.OS([O-])(=O)=O.[K+]>O>[Cl:41][C:27]1[C:28]([CH2:33][NH:34][C:35](=[O:40])[C:36]([CH3:37])([CH3:38])[CH3:39])=[CH:29][CH:30]=[C:31]([Cl:32])[C:26]=1[NH:25][C:23]1[N:22]([CH3:42])[C:9]2=[N:10][C:11]([N:12]3[CH2:13][CH2:14][CH:15]([C:18]([F:19])([F:20])[F:21])[CH2:16][CH2:17]3)=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[C:8]2[N:24]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 516920Potassium bisulfateHCID 67957833HCID 67957833, compound

Product 1

HCID 67958121HCID 67958121, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-5-[4-trifluoromethyl-piperidinyl]-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl ester (3.85 g, 6.1 mmol) 2 N NaOH (12 mL, 24 mmol) and 60 mL EtOH is stirred for 4.5 h at 55° C. and overnight at rt. Then the mixture is poured into 150 mL water, the mixture is acidified to pH ˜5.5 with aq. KHSO4 and the mixture is concentrated. The resulting precipitate is collected by filtration and dried. Yield: 1.44 g. HPLC Rt=1.47 min (method D). MS m/z: 599 [M+H]+.

Workup

  1. concentrationthe mixture is concentrated
  2. filtrationThe resulting precipitate is collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-3b944694b71647b3bfbd612a779b86c6
Source dataset
uspto-grants-2013_07
Patent number
US08486968B2

Reaction notes

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