Sodium Hydroxide → 4-(2-Fluoro-4-iodophenylamino)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1[C:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=2[F:32])=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:9]2=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+]>>[F:32][C:26]1[CH:27]=[C:28]([I:31])[CH:29]=[CH:30][C:25]=1[NH:24][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[C:9]2[N:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[N:13]=[CH:14][C:8]=12Participants
3
Conditions
- Temperature
- 65 °C
Procedure
To a suspension of 4-(2-fluoro-4-iodophenylamino)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (380 mg, 0.71 mmol) in IMS (10 mL) was added aqueous sodium hydroxide solution (1.78 mL, 1M, 1.78 mmol). The reaction mixture was heated at 65° C. for 2 hours, during which time all solids dissolved. Volatile solvents were removed in vacuo and the resultant solution was acidified to pH ˜3 by careful addition of aqueous hydrochloric acid (1M) causing a precipitate to form. The precipitate was collected by filtration and dried under vacuum at 45° C. to yield the title compound as a brown solid (360 mg, 100%). LCMS (Method B): RT=3.84 min, [M+H]+=519.
Workup
- dissolutiondissolved
- customVolatile solvents were removed in vacuo
- additionthe resultant solution was acidified to pH ˜3 by careful addition of aqueous hydrochloric acid (1M)
- customto form
- filtrationThe precipitate was collected by filtration
- customdried under vacuum at 45° C.
Sources & evidence
- ORD record
- ord-eb8761516ad5489fb6369aa9d18d5f5a
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841462B2
Reaction notes
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