4-Phenethylpiperazin-2-one → tert-Butyl 7-(2-oxo-4-phenethylpiperazin-1-yl)-5-tosyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 2365403Notes

Reaction equation

HRID 2365403 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][CH2:21][C:7]=3[N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9]=2[CH:10]=1.[CH2:32]([N:40]1[CH2:45][CH2:44][NH:43][C:42](=[O:46])[CH2:41]1)[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[O:46]=[C:42]1[CH2:41][N:40]([CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:45][CH2:44][N:43]1[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][CH2:21][C:7]=3[N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9]=2[CH:10]=1

Participants

3

Reactant 2

HCID 85471654-Phenethylpiperazin-2-oneHCID 57950411tert-butyl 7-bromo-5-tosyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 67986824tert-Butyl 7-(2-oxo-4-phenethylpiperazin-1-yl)-5-tosyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylateYield 60.1%

Procedure

tert-Butyl 7-bromo-5-tosyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (600 mg, 1.19 mmol) and 4-phenethylpiperazin-2-one (266 mg, 1.30 mmol) were reacted according to Example 2 (step f) to provide the title compound (450 mg, 60%) as a white powder: ESI MS m/z 629 [M+H]+.

Sources & evidence

ORD record
ord-c4777f18f6204753905697fd28390cee
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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