Ammonia → HCID 59278121, compound

HRID 559704Notes

Reaction equation

HRID 559704 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([CH:11]([NH:14][C:15]([C:17]2[C:18]3[CH:25]=[N:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:19]=3[CH:20]=[N:21][CH:22]=2)=[O:16])[CH2:12][CH3:13])[O:8][C:9]=1[CH3:10])=O.[NH3:33].CO>>[C:3]([C:5]1[N:6]=[C:7]([CH:11]([NH:14][C:15]([C:17]2[C:18]3[CH:25]=[N:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:19]=3[CH:20]=[N:21][CH:22]=2)=[O:16])[CH2:12][CH3:13])[O:8][C:9]=1[CH3:10])(=[O:2])[NH2:33]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 59278232HCID 59278232, compound

Product 1

HCID 59278121HCID 59278121, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(1-{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-propyl)-5-methyl-oxazole-4-carboxylic acid methyl ester (40 mg, 0.091 mmol) in a 7 M solution of ammonia in methanol (525 μL, 3.66 mmol) was stirred at 90° C. in a sealed tube. After 34 hours, the reaction was cooled to room temperature, vented, opened and concentrated. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-10% methanol in methylene chloride to afford the title compound as white solid. MS m/z 423.89 (MH+).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. concentrationconcentrated
  3. customThe resulting residue was purified by silica gel chromatography
  4. washeluting with a gradient of 0-10% methanol in methylene chloride

Sources & evidence

ORD record
ord-eef75aced9a7463fbf0667d5d37656cd
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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