4-(2-(Pyridin-2-yl)ethyl)piperazin-2-one → tert-Butyl 6-methyl-8-(2-oxo-4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate

HRID 474954Notes

Reaction equation

HRID 474954 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][CH2:12][C:7]=3[N:8]([CH3:11])[C:9]=2[CH:10]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][NH:35][C:34](=[O:38])[CH2:33]1>>[CH3:11][N:8]1[C:9]2[CH:10]=[C:2]([N:35]3[CH2:36][CH2:37][N:32]([CH2:31][CH2:30][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=4)[CH2:33][C:34]3=[O:38])[CH:3]=[CH:4][C:5]=2[C:6]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][CH2:12][C:7]1=2

Participants

3

Reactant 2

HCID 580934314-(2-(Pyridin-2-yl)ethyl)piperazin-2-oneHCID 66874851tert-Butyl 8-bromo-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate

Product 1

HCID 70805251tert-Butyl 6-methyl-8-(2-oxo-4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylateYield 20%

Procedure

tert-Butyl 8-bromo-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (200 mg, 0.528 mmol) and 4-(2-(pyridin-2-yl)ethyl)piperazin-2-one (118 mg, 0.576 mmol) were reacted following the procedure for Example 53 (step b) to provide the title compound (52 mg, 20%) as a white solid: ESI MS m/z 504 [M+H]−.

Sources & evidence

ORD record
ord-7b56dd9647044c9e82cffb4e5f0fb1bc
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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