Potassium Carbonate → N-Cyclopropyl-4-methyl-3-(1-oxo-2-(1-phenylethyl)-1,2-dihydroisoquinolin-6-yl)benzamide

HRID 907348Notes

Reaction equation

[CH:1]1([NH:4][C:5](=[O:24])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[NH:18][CH:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:33]>CN(C=O)C>[CH:1]1([NH:4][C:5](=[O:24])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH3:33])[CH:17]=[CH:16]4)[CH:7]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of the product of Example 11 (200 mg), potassium carbonate (260 mg) and (1-bromoethyl)benzene (0.100 mL) in DMF (2 mL) was stirred at 80° C. for 17 hours. Further (1-bromoethyl)benzene (0.100 mL) and potassium carbonate (260 mg) was added and stirred at 80° C. for a further 24 hours. Additional (1-bromoethyl)benzene (0.5 mL) and potassium carbonate (500 mg) were added and the reaction stirred at 80° C. for a further 48 hours. The reaction mixture was filtered and purified by HPLC to yield the title compound (14 mg) as a solid.

Workup

stirringstirred at 80° C. for a further 24 hours
stirringthe reaction stirred at 80° C. for a further 48 hours
filtrationThe reaction mixture was filtered
custompurified by HPLC

Sources & evidence

ORD record: ord-7319f5d5351a4a589f1f4d2e54684a58
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012979B2

Reaction notes

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