m-Chloroperbenzoic acid → HCID 23156868, compound

HRID 1098300Notes

Reaction equation

[N:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[C:12]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:24]([F:27])([F:26])[F:25])[NH:13][C:14]3=[O:17])=[CH:9][CH:8]=2)[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:36])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:36]=[S:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[C:12]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:24]([F:27])([F:25])[F:26])[NH:13][C:14]3=[O:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

20.1 mg (0.0515 mmol) of the 7-thiomorpholin-4-yl-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in Example 104 was dissolved in 2.3 ml of methylene chloride, and 9.8 mg (0.0566 mmol) of m-chloroperbenzoic acid was further added to the solution. The obtained mixture was stirred at 0° C. for 2 hours. Thereafter, a saturated sodium bicarbonate aqueous solution was added to the reaction solution, and the obtained mixture was then extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate, and was then concentrated. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=20:1), so as to obtain 16.6 mg (79%) of 7-(1-oxothiomorpholin-4-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one in the form of a light yellow solid.

Workup

extractionthe obtained mixture was then extracted with methylene chloride
dry with materialThe extract was dried over anhydrous sodium sulfate
concentrationwas then concentrated
customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=20:1)

Sources & evidence

ORD record: ord-12e510b113ff47dabb3aa4375b301fa8
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143274B2

Reaction notes

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