5-Amino-1-butyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one → N-(1-Butyl-3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-3-(4-isopropoxy-phenyl)-propionamide

HRID 2235399Notes

Reaction equation

HRID 2235399 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[N:7]([CH2:14][CH2:15][CH2:16][CH3:17])[C:6](=[O:18])[C:5]2([CH3:20])[CH3:19].[CH:21]([O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33](Cl)=[O:34])=[CH:27][CH:26]=1)([CH3:23])[CH3:22]>>[CH2:14]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][C:33](=[O:34])[CH2:32][CH2:31][C:28]3[CH:29]=[CH:30][C:25]([O:24][CH:21]([CH3:22])[CH3:23])=[CH:26][CH:27]=3)=[C:10]([N+:11]([O-:13])=[O:12])[CH:9]=2)[C:5]([CH3:19])([CH3:20])[C:6]1=[O:18])[CH2:15][CH2:16][CH3:17]

Participants

3

Reactant 2

HCID 178027335-Amino-1-butyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-oneHCID 230926883-(4-Isopropoxy-phenyl)-propionyl chloride

Product 1

HCID 23092663N-(1-Butyl-3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-3-(4-isopropoxy-phenyl)-propionamide

Procedure

N-(1-Butyl-3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-3-(4-isopropoxy-phenyl)-propionamide is prepared from A4 (500 mg) and 3-(4-isopropoxy-phenyl)-propionyl chloride (1.01 g; 5.5 mmol) as described in Example 1a. The crude material is purified by flash chromatography eluting with light petroleum/EtOAc (6:1) to give the compound (791 mg).

Workup

  1. customThe crude material is purified by flash chromatography
  2. washeluting with light petroleum/EtOAc (6:1)

Sources & evidence

ORD record
ord-0db4f3a1f0e8408882c18baa5629bd3b
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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