Isobutyric Acid → HCID 64088099, compound

HRID 1467967Notes

Reaction equation

HRID 1467967 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH2:10])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[C:40](O)(=[O:44])[CH:41]([CH3:43])[CH3:42]>CN(C=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:40](=[O:44])[CH:41]([CH3:43])[CH3:42])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 5

HCID 6590Isobutyric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 788675-AminoindoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 64088099HCID 64088099, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-Indole amine (0.5 g, 3.78 mmol), 1-ethyl-3(3-dimethylaminopropyl)carbodiimidehydrochloride (1.45 g, 7.56 mmol), 1-hyroxybenzotriazole (0.578 g, 3.78 mmol) in anhydrous DMF (25 mL), triethylamine (1.0 mL, 7.5 mmol) and isobutyric acid (0.31 mL, 3.4 mmol) were added and stirred at room temperature for 12 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the resultant residue was purified by flash column chromatography to give N-(1H-indol-5-yl)isobutyramide (0.596 g, 77.8%); MS: 203.1 (M+1)

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe resultant residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-3e8518961a9543cebc4816a02eb55bf3
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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