Acetic Acid → 7-tetrazol-1-yl-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1098304Notes

Reaction equation

C(OC)(OC)OC.[N-:8]=[N+:9]=[N-:10].[Na+].[C:12](O)(=O)C.[NH2:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[C:22]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:36])[F:35])[NH:23][C:24]2=[O:27])=[CH:19][CH:18]=1>O>[N:16]1([C:17]2[CH:26]=[C:25]3[C:20]([CH:21]=[C:22]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([F:37])([F:35])[F:36])[NH:23][C:24]3=[O:27])=[CH:19][CH:18]=2)[CH:12]=[N:10][N:9]=[N:8]1

Participants

Conditions

Temperature: 80 °C

Procedure

17.5 μl (0.16 mmol) of trimethyl orthoformate and 9.8 mg (0.15 mmol) of sodium azide were added to 0.2 ml of an acetic acid solution containing the 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in Example 38. The obtained mixture was stirred at 80° C. for 6 hours. Thereafter, the reaction solution was cooled to a room temperature, and water was then added to thereto, followed by extraction with ethyl acetate. The extract was washed with a saturated sodium bicarbonate aqueous solution, and was then dried over anhydrous sodium sulfate, followed by concentration. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1), so as to obtain 29.8 mg (83%) of 7-tetrazol-1-yl-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one in the form of a colorless solid.

Workup

temperatureThereafter, the reaction solution was cooled to a room temperature
extractionfollowed by extraction with ethyl acetate
washThe extract was washed with a saturated sodium bicarbonate aqueous solution
dry with materialwas then dried over anhydrous sodium sulfate
concentrationfollowed by concentration
customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record: ord-43eefd375f8e43ee8c9df84003f3c8ec
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143274B2

Reaction notes

Loading…