Dichloromethane methanol → HCID 86640825, compound

HRID 1929686Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:18][CH3:19])=[N:15][C:16](I)=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([C:29]([F:32])([F:31])[F:30])=[C:24]([F:33])[CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)[Cl:35].CO>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:18][CH3:19])=[N:15][C:16]([Cl:35])=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([C:29]([F:32])([F:31])[F:30])=[C:24]([F:33])[CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 21226129Dichloromethane methanol

HCID 66734085HCID 66734085, compound

Product 1

HCID 86640825HCID 86640825, compound

Procedure

According to the general procedure (GP12), chlorination of 8-[2-(3,5-difluoro-4-trifluoromethyl-phenyl)-ethyl]-3-ethyl-1-iodo-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (500 mg; 0.854 mmol) and purification by FC (DCM/MeOH=100/3) gave the product 1-chloro-8-[2-(3,5-difluoro-4-trifluoromethyl-phenyl)-ethyl]-3-ethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow solid (179 mg; 42%). LC-MS: tR=1.05 min.; [M+H]+=494.37 g/mol.

Sources & evidence

ORD record: ord-0c6f1aee830d4745900f20111481aee5
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188082B2

Reaction notes

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