Dichloromethane methanol → N-{3-[2-(7,7-dimethyl-6-oxo-5-pentyl-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-ethyl]-phenyl}-acetamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([NH:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][C:21]=2[N+:22]([O-])=O)[N:18]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:17](=[O:30])[C:16]3([CH3:32])[CH3:31])=O)[CH:5]=[CH:6][CH:7]=1.[CH2:33](Cl)Cl.[CH3:36][OH:37]>>[CH3:31][C:16]1([CH3:32])[C:15]2[CH:14]=[C:13]3[NH:12][C:10]([CH2:9][CH2:8][C:4]4[CH:3]=[C:2]([NH:1][C:36](=[O:37])[CH3:33])[CH:7]=[CH:6][CH:5]=4)=[N:22][C:21]3=[CH:20][C:19]=2[N:18]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:17]1=[O:30]Participants
3
Procedure
N-{3-[2-(7,7-Dimethyl-6-oxo-5-pentyl-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-ethyl]-phenyl}-acetamide is prepared from 3-(3-amino-phenyl)-N-(3,3-dimethyl-6-nitro-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-propionamide as described in Example 3b. Under the microwave conditions the acetylated product is formed. The desired N-{3-[2-(7,7-dimethyl-6-oxo-5-pentyl-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-ethyl]-phenyl}-acetamide (229 mg) is obtained by flash chromatography on silica gel eluting with CH2Cl2/MeOH (99:1).
Workup
- customUnder the microwave conditions the acetylated product is formed
Sources & evidence
- ORD record
- ord-32d28b08b9dd4683a5108693eb576dfb
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07714010B2
Reaction notes
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