Dichloromethane methanol → HCID 66734009, compound

HRID 1929689Notes

Reaction equation

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

Participants

Reactant 2

HCID 21226129Dichloromethane methanol

HCID 66734170HCID 66734170, compound

Product 1

HCID 66734009HCID 66734009, compound

Procedure

According to the general procedure (GP12), chlorination of 8-[2-(3,4-dimethyl-phenyl)-ethyl]-1-iodo-3-methyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (1.061 g; 2.142 mmol) and purification by FC (DCM/MeOH=40/1) gave the product 1-chloro-8-[2-(3,4-dimethyl-phenyl)-ethyl]-3-methyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as an orange oil (157 mg; 0.388 mmol). LC-MS: tR=1.01 min.; [M+H]+=404.50 g/mol.

Sources & evidence

ORD record: ord-4976b8a636844c0989547ca1c1441271
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188082B2

Reaction notes

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