N-(3,3-Dimethyl-6-nitro-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-N-methyl-3-phenyl-propionamide → 1,7,7-Trimethyl-5-pentyl-2-phenethyl-5,7-dihydro-1h-imidazo[4,5-f]indol-6-one

HRID 2235414Notes

Reaction equation

HRID 2235414 reaction equation
[CH3:1][C:2]1([CH3:32])[C:10]2[C:5](=[CH:6][C:7]([N+:23]([O-])=O)=[C:8]([N:11]([CH3:22])[C:12](=O)[CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=2)[N:4]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:3]1=[O:31]>C(Cl)Cl.CO>[CH3:22][N:11]1[C:8]2=[CH:9][C:10]3[C:2]([CH3:1])([CH3:32])[C:3](=[O:31])[N:4]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:5]=3[CH:6]=[C:7]2[N:23]=[C:12]1[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 1

HCID 23092651N-(3,3-Dimethyl-6-nitro-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-N-methyl-3-phenyl-propionamide

Product 1

HCID 593009231,7,7-Trimethyl-5-pentyl-2-phenethyl-5,7-dihydro-1h-imidazo[4,5-f]indol-6-one

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

1,7,7-Trimethyl-5-pentyl-2-phenethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one is prepared from crude N-(3,3-dimethyl-6-nitro-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-N-methyl-3-phenyl-propionamide as described in Example 3b. The desired compound (78 mg) is obtained by flash chromatography on silica gel eluting with CH2Cl2/MeOH (98:2).

Sources & evidence

ORD record
ord-59f80d1bf6c94d8ba05bc6cb19645faa
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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