Ammonia → HCID 52917425, compound

HRID 2172976Notes

Reaction equation

HRID 2172976 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2([NH:13][C:14]([C:16]3[C:17]4[CH:24]=[N:23][N:22]([C:25]5[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=5)[C:18]=4[CH:19]=[N:20][CH:21]=3)=[O:15])[CH2:12][CH2:11]2)[CH:5]=1.[NH3:33].CO>>[C:3]([C:4]1[CH:5]=[C:6]([C:10]2([NH:13][C:14]([C:16]3[C:17]4[CH:24]=[N:23][N:22]([C:25]5[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=5)[C:18]=4[CH:19]=[N:20][CH:21]=3)=[O:15])[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1)(=[O:2])[NH2:33]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 52916888HCID 52916888, compound

Product 1

HCID 52917425HCID 52917425, compound

Procedure

A solution of 3-(1-{[1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-cyclopropyl)-benzoic acid methyl ester (70.0 mg, 0.163 mmol) in a 7M solution of ammonia in methanol (1.00 mL, 7.00 mmol) is stirred at 120° C. in a sealed pressure tube. After 78 hours, the reaction vessel is cooled to room temperature, vented and opened. The reaction mixture is concentrated in vacuo, and the resulting residue is purified by silica gel chromatography eluting with a gradient of 0-10% methanol in methylene chloride to afford the title compound a solid.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe resulting residue is purified by silica gel chromatography
  3. washeluting with a gradient of 0-10% methanol in methylene chloride

Sources & evidence

ORD record
ord-cf961e0940c44320bf9e2507fd09ff0b
Source dataset
uspto-grants-2015_06
Patent number
US09056858B2

Reaction notes

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