Acetic Anhydride → HCID 59189839, compound

HRID 216643Notes

Reaction equation

HRID 216643 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[NH2:8][C:9]([NH:11][C:12]1[NH:13][C:14]2[C:19]([C:20]=1[C:21]([NH2:23])=[O:22])=[CH:18][CH:17]=[C:16]([C:24]1[CH:29]=C[CH:27]=[C:26](CO)[CH:25]=1)[CH:15]=2)=[O:10]>N1C=CC=CC=1>[C:5]([O:4][CH2:1][C:2]1[CH:29]=[C:24]([C:16]2[CH:15]=[C:14]3[C:19]([C:20]([C:21]([NH2:23])=[O:22])=[C:12]([NH:11][C:9]([NH2:8])=[O:10])[NH:13]3)=[CH:18][CH:17]=2)[CH:25]=[CH:26][CH:27]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 24989422HCID 24989422, compound2×

Product 1

HCID 59189839HCID 59189839, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Pyridine (4 mL) and acetic anhydride (61 μL, 0.65 mmol) were added to 2-aminocarbonylamino-6-(3-hydroxymethylphenyl)indole-3-carboxamide (Compound 12-1, 0.18 g, 0.55 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and water (10 mL) was added to the residue. The precipitated solid was separated by filtration. The resultant solid was washed with water (10 mL) and dried under reduced pressure to give the title compound (0.17 g) as a slightly brown solid (yield 87%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water (10 mL)
  2. additionwas added to the residue
  3. customThe precipitated solid was separated by filtration
  4. washThe resultant solid was washed with water (10 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-1e5cd5618a4547168b60a22138f6fca6
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Reaction notes

Loading…