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

HRID 1677687Notes

Reaction equation

HRID 1677687 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-b791e3cfceea47258e7d4e83d5a1977d
Source dataset
uspto-grants-2011_08
Patent number
US08008327B2

Reaction notes

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