Water → 2-Aminocarbonylamino-6-(1-hydroxyethyl)indole-3-carboxamide

HRID 216635Notes

Reaction equation

HRID 216635 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:19]([NH2:21])=[O:20])=[C:11]([NH:15][C:16]([NH2:18])=[O:17])[NH:12]2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4].O>O1CCCC1>[NH2:18][C:16]([NH:15][C:11]1[NH:12][C:13]2[C:9]([C:10]=1[C:19]([NH2:21])=[O:20])=[CH:8][CH:7]=[C:6]([CH:3]([OH:5])[CH3:4])[CH:14]=2)=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 591897756-Acetyl-2-aminocarbonylaminoindole-3-carboxamide

Product 1

HCID 591898862-Aminocarbonylamino-6-(1-hydroxyethyl)indole-3-carboxamideYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (10 mg, 0.26 mmol) was added to a solution of 6-acetyl-2-aminocarbonylaminoindole-3-carboxamide (Compound 14-1,14 mg, 0.054 mmol) in anhydrous tetrahydrofuran (2 mL) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. Water (5 mL) was added to the reaction mixture, and the whole was extracted with ethyl acetate (20 mL). The organic layer was washed with brine (5 mL), and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resultant solid was washed with diethyl ether (2 mL) and dried under reduced pressure to give the title compound (3 mg) as a colorless solid (yield 22%).

Workup

  1. temperaturecooling
  2. extractionthe whole was extracted with ethyl acetate (20 mL)
  3. washThe organic layer was washed with brine (5 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. washthe resultant solid was washed with diethyl ether (2 mL)
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c3ede20c1faf4393a8be07f577c14b7f
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Reaction notes

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