Dichloromethane methanol → HCID 66733978, compound

HRID 1929700Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:17][CH2:18][CH3:19])=[N:15][CH:16]=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[C:24]([F:32])[CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)[Cl:34].CO>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:17][CH2:18][CH3:19])=[N:15][C:16]([Cl:34])=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:31])[F:29])=[C:24]([F:32])[CH:23]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 21226129Dichloromethane methanol

HCID 66733794HCID 66733794, compound

Product 1

HCID 66733978HCID 66733978, compound

Procedure

Subsequent chlorination (70° C.; 3h30) of 8-[2-(3-fluoro-4-trifluoromethyl-phenyl)-ethyl]-3-propyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (2.310 g; 5.071 mmol), and purification by FC (DCM/MeOH=50/1) afforded 1-chloro-8-[2-(3-fluoro-4-trifluoromethyl-phenyl)-ethyl]-3-propyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow oil (1.130 g; 45%). LC-MS: tR=1.10 min.; [M+H]+=489.94 g/mol.

Sources & evidence

ORD record: ord-87c3b67154cc46408bc509cf279d43f6
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188082B2

Reaction notes

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