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

HRID 882049Notes

Reaction equation

HRID 882049 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH3:23])[C:9]3[CH2:14][CH:13]([CH3:15])[N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:10]=3[C:5]2=[CH:4][CH:3]=1.[F:24][C:25]1[CH:39]=[CH:38][C:28]([CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][NH:34][C:33](=[O:37])[CH2:32]2)=[CH:27][CH:26]=1>>[CH3:15][CH:13]1[N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:10]2[C:5]3[C:6]([N:8]([CH3:23])[C:9]=2[CH2:14]1)=[N:7][C:2]([N:34]1[CH2:35][CH2:36][N:31]([CH2:30][CH2:29][C:28]2[CH:38]=[CH:39][C:25]([F:24])=[CH:26][CH:27]=2)[CH2:32][C:33]1=[O:37])=[CH:3][CH:4]=3

Participants

3

Reactant 2

HCID 575147614-(4-Fluorophenethyl)piperazin-2-oneHCID 86667082tert-Butyl 2-bromo-7,9-dimethyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridine-6-carboxylate

Product 1

HCID 67988842tert-Butyl 7,9-dimethyl-2-(2-oxo-4-(4-fluorophenethyl)piperazin-1-yl)-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridine-6-carboxylateYield 73%

Procedure

tert-Butyl 2-bromo-7,9-dimethyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (2-((4 mg, 0.640 mmol) and 4-(4-fluorophenethyl)piperazin-2-one (141 mg, 0.640 mmol) were reacted following the procedure for Example 2 (step e) to provide the title compound (245 mg, 73%) as a colorless oil: ESI MS m/z 522 [M+H]+.

Sources & evidence

ORD record
ord-a5180d339dc045f4ac26514197b48329
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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