Methanol → 2-Aminocarbonylamino-6-hydroxymethylindole-3-carboxamide
Reaction equation
CCCCCC.[H-].C([Al+]CC(C)C)C(C)C.[NH2:17][C:18]([NH:20][C:21]1[NH:22][C:23]2[C:28]([C:29]=1[C:30]([NH2:32])=[O:31])=[CH:27][CH:26]=[C:25]([C:33](OC)=[O:34])[CH:24]=2)=[O:19].O.CO>O1CCCC1>[NH2:17][C:18]([NH:20][C:21]1[NH:22][C:23]2[C:28]([C:29]=1[C:30]([NH2:32])=[O:31])=[CH:27][CH:26]=[C:25]([CH2:33][OH:34])[CH:24]=2)=[O:19]Participants
6
Procedure
1.0 M Diisobutylaluminium hydride hexane solution (68 mL, 68 mmol) was added to a solution of 2-aminocarbonylamino-6-methoxycarbonylindole-3-carboxamide (Compound 2-17, 4.0 g, 15 mmol) in anhydrous tetrahydrofuran (50 mL) under ice-cooling, and the mixture was stirred at room temperature for 3.5 hours. Water (2 mL) and methanol (20 mL) were added to the reaction mixture, and the mixture was filtered throught Celite® pad with methanol (200 mL) and 1,4-dioxane (200 mL). After the solvent was evaporated under reduced pressure, the resultant solid was washed with diethyl ether (10 mL) and dried under reduced pressure to give the title compound (2.3 g) as a yellow solid (yield 63%).
Workup
- temperaturecooling
- filtrationthe mixture was filtered
- customAfter the solvent was evaporated under reduced pressure
- washthe resultant solid was washed with diethyl ether (10 mL)
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-0b18e5c88c8f400e9c375085ecdda254
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193237B2
Reaction notes
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