Methanol → HCID 52916890, compound

HRID 2172977Notes

Reaction equation

HRID 2172977 reaction equation
CO[C:3](=[O:32])[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.[CH3:33][NH2:34].CO>>[CH3:33][NH:34][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:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=5)[C:18]=4[CH:19]=[N:20][CH:21]=3)=[O:15])[CH2:11][CH2:12]2)[CH:7]=[CH:8][CH:9]=1)=[O:32]

Participants

4

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 52916888HCID 52916888, compound

Product 1

HCID 52916890HCID 52916890, compound

Conditions

Temperature
90 °C

Procedure

A mixture 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 2M solution of methylamine in methanol (3.0 mL, 6.0 mmol) is stirred at 90° C. in a sealed pressure tube. After 18 hours, the reaction vessel is cooled to room temperature, vented and opened. The reaction mixture is concentrated in vacuo. The residue is purified by silica gel chromatography eluting with a gradient of 0-8% methanol in methylene chloride to afford the title compound as a solid.

Workup

  1. temperaturethe reaction vessel is cooled to room temperature
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customThe residue is purified by silica gel chromatography
  4. washeluting with a gradient of 0-8% methanol in methylene chloride

Sources & evidence

ORD record
ord-f52f879ae17448fbbd2cdfc227eed9b4
Source dataset
uspto-grants-2015_06
Patent number
US09056858B2

Reaction notes

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