Chlorosuccinimide → HCID 66734435, compound

HRID 1929708Notes

Reaction equation

[Cl:1]N1C(=O)CCC1=O.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]2[C:22]([CH:25]([CH3:27])[CH3:26])=[N:23][CH:24]=[C:18]2[CH:17]1[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>C(Cl)(Cl)Cl.C(Cl)Cl>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]2[C:22]([CH:25]([CH3:27])[CH3:26])=[N:23][C:24]([Cl:1])=[C:18]2[CH:17]1[CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]([F:37])([F:38])[F:39])=[CH:34][CH:35]=1)=[O:15])([CH3:11])([CH3:12])[CH3:10]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of N-chlorosuccinimide (87.3 mg; 0.628 mmol) in chloroform (1 ml) was added a solution of 3-isopropyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (229 mg; 0.523 mmol) in chloroform (2 ml) and the resulting solution was heated to 70° C. for 5 h30. The reaction mixture was allowed to cool to rt, diluted with DCM (20 ml) and washed with water (3×10 ml). The organic layer was dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by preparative HPLC gave the pure product 1-chloro-3-isopropyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow solid (97 mg; 39%). LC-MS: tR=1.04 min.; [M+H]+=472.51 g/mol.

Workup

temperatureto cool to rt
washwashed with water (3×10 ml)
dry with materialThe organic layer was dried over anh. MgSO4
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure
customPurification by preparative HPLC

Sources & evidence

ORD record: ord-865b01ad672b426d83ea338ce2fe049e
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188082B2

Reaction notes

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