Ammonia → 1-(4-Fluoro-phenyl)-1H-indazole-4-carboxylic acid (6-carbamoyl-pyridin-3-ylmethyl)-amide

HRID 2382941Notes

Reaction equation

HRID 2382941 reaction equation
C(O[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14]([C:16]2[C:17]3[CH:18]=[N:19][N:20]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[C:21]=3[CH:22]=[CH:23][CH:24]=2)=[O:15])=[CH:8][N:7]=1)=[O:5])C.[NH3:32].CO>>[C:4]([C:6]1[N:7]=[CH:8][C:9]([CH2:12][NH:13][C:14]([C:16]2[C:17]3[CH:18]=[N:19][N:20]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[C:21]=3[CH:22]=[CH:23][CH:24]=2)=[O:15])=[CH:10][CH:11]=1)(=[O:5])[NH2:32]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 581389055-({[1-(4-Fluoro-phenyl)-1H-indazole-4-carbonyl]-amino}-methyl)-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 581389041-(4-Fluoro-phenyl)-1H-indazole-4-carboxylic acid (6-carbamoyl-pyridin-3-ylmethyl)-amide

Procedure

A solution of 5-({[1-(4-fluoro-phenyl)-1H-indazole-4-carbonyl]-amino}-methyl)-pyridine-2-carboxylic acid ethyl ester (Example 5) (60 mg, 0.1 mmol) in a 7 N solution of ammonia in methanol (0.65 mL, 4.6 mmol) was stirred at 100° C. in a sealed tube for 16 hours. The mixture was cooled to room temperature and filtered. The solid was washed with MeOH (3×3 mL) and dried. The solid was then triturated with ethyl acetate (2 mL), sonicated, filtered and air dried to afford the title compound.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with MeOH (3×3 mL)
  3. customdried
  4. customThe solid was then triturated with ethyl acetate (2 mL)
  5. customsonicated
  6. filtrationfiltered
  7. customair dried

Sources & evidence

ORD record
ord-3bcb3b400e8e43a9808d5bc4c5c4b1c4
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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