Dichloromethane methanol → HCID 66734040, compound

HRID 1929698Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:17][CH3:18])=[N:15][CH:16]=[C:10]2[CH:9]1[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)[Cl:33].CO>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:17][CH3:18])=[N:15][C:16]([Cl:33])=[C:10]2[CH:9]1[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[CH:25][CH:26]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 21226129Dichloromethane methanol

HCID 66733623HCID 66733623, compound

Product 1

HCID 66734040HCID 66734040, compound

Procedure

Subsequent chlorination (70° C.; 4h30) of 3-ethyl-8-[2-(4-trifluoromethoxy-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (1.200 g; 2.731 mmol), and purification by FC (DCM/MeOH=50/1) afforded 1-chloro-3-ethyl-8-[2-(4-trifluoromethoxy-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow oil (0.810 g; 63%). LC-MS: tR=1.08 min.; [M+H]+=473.97 g/mol.

Sources & evidence

ORD record: ord-77c3b08c7bd345b3a7932934b5a363d1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188082B2

Reaction notes

Loading…