Dichloromethane methanol → HCID 66734164, compound

HRID 1929699Notes

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])=[CH:24][CH:23]=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][CH2:18][CH3:19])=[N:15][C:16]([Cl:33])=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 21226129Dichloromethane methanol

HCID 66734091HCID 66734091, compound

Product 1

HCID 66734164HCID 66734164, compound

Procedure

Subsequent chlorination (70° C.; 3h30) of 3-propyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (2.940 g; 6.720 mmol), and purification by FC (DCM/MeOH=25/1) afforded 1-chloro-3-propyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow oil (1.550 g; 49%). LC-MS: tR=1.09 min.; [M+H]+=472.00 g/mol.

Sources & evidence

ORD record: ord-cb7e7a7ac8f0407db8cfb09d185ef975
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188082B2

Reaction notes

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