Dichloromethane methanol → HCID 66733884, compound

HRID 1929697Notes

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]=[C:25]([F:27])[C:24]([O:28][CH3:29])=[C:23]([F:30])[CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)[Cl:32].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:32])=[C:10]2[CH:9]1[CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([F:30])[C:24]([O:28][CH3:29])=[C:25]([F:27])[CH:26]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 21226129Dichloromethane methanol

HCID 66733885HCID 66733885, compound

Product 1

HCID 66733884HCID 66733884, compound

Procedure

Subsequent chlorination (70° C.; 3h30) of 8-[2-(3,5-difluoro-4-methoxy-phenyl)-ethyl]-3-ethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (1.330 g; 3.156 mmol), and purification by FC (DCM/MeOH=25/1) afforded 1-chloro-8-[2-(3,5-difluoro-4-methoxy-phenyl)-ethyl]-3-ethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow oil (0.730 g; 51%). LC-MS: tR=1.04 min.; [M+H]+=456.05 g/mol.

Sources & evidence

ORD record: ord-6338dff07da64365a4c8fc2157976816
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188082B2

Reaction notes

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