4-Phenethylpiperazin-2-one → tert-Butyl 9-methyl-2-(2-oxo-4-phenethylpiperazin-1-yl)-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridine-6-carboxylate

HRID 882019Notes

Reaction equation

HRID 882019 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH3:22])[C:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C:10]=3[C:5]2=[CH:4][CH:3]=1.[CH2:23]([N:31]1[CH2:36][CH2:35][NH:34][C:33](=[O:37])[CH2:32]1)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH3:22][N:8]1[C:6]2=[N:7][C:2]([N:34]3[CH2:35][CH2:36][N:31]([CH2:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:32][C:33]3=[O:37])=[CH:3][CH:4]=[C:5]2[C:10]2[CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14][C:9]1=2

Participants

3

Reactant 2

HCID 85471654-Phenethylpiperazin-2-oneHCID 71551310tert-Butyl 2-bromo-9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridine-6-carboxylate

Product 1

HCID 67988824tert-Butyl 9-methyl-2-(2-oxo-4-phenethylpiperazin-1-yl)-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridine-6-carboxylateYield 67.5%

Procedure

tert-Butyl 2-bromo-9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (86 mg, 0.23 mmol) and 4-phenethylpiperazin-2-one (56 mg, 0.27 mmol) were reacted according to Example 2 (step e) to provide the title compound (76 mg, 67%) as a yellow powder: ESI MS m/z 490 [M+H]+.

Sources & evidence

ORD record
ord-6249e7dac6804b33874edce322f987d6
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

Loading…