Acetic Acid → 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1H-indazole-5-carboxylic acid

HRID 2064630Notes

Reaction equation

HRID 2064630 reaction equation
Cl.Cl.[CH3:3][C:4]1[C:23]([CH3:24])=[CH:22][C:7]2[NH:8][C:9]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=C(C#N)[CH:18]=4)[NH:13][N:12]=3)=[N:10][C:6]=2[CH:5]=1.[C:25]([OH:28])(=[O:27])[CH3:26]>>[CH3:24][C:23]1[C:4]([CH3:3])=[CH:5][C:6]2[NH:10][C:9]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:26]([C:25]([OH:28])=[O:27])[CH:18]=4)[NH:13][N:12]=3)=[N:8][C:7]=2[CH:22]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 1363343463-(5,6-Dimethyl-1H-benzoimidazol-2-yl)-1H-indazole-5-carbonitrile Dihydrochloride

Product 1

HCID 1358046313-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1H-indazole-5-carboxylic acid

Conditions

Temperature
100 °C

Procedure

A stirred suspension of 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1H-indazole-5-carbonitrile dihydrochloride [200 mg, Reference Example 6(aq)] in acetic acid/concentrated hydrochloric acid (4 ml, 1:1 v/v) was heated at 100° C. for 16 hours. The reaction mixture was cooled to ambient temperature and filtered. The precipitate was washed with water and dried in vacuo to give 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1H-indazole-5-carboxylic acid (195 mg) as a white solid. LC-MS (METHOD B): RT=2.52 minutes, 307 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. washThe precipitate was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e5abfb3f6427473a840c4644f37683c8
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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