Benzenesulfonyl chloride → HCID 56651012, compound

HRID 1191312Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]4[CH:21]=[CH:20][CH:19]=[CH:18][C:14]4=[CH:15][CH:16]=3)[NH:11][C:10](=[O:22])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1>[O:22]=[C:10]1[N:9]=[C:8]([C:4]2[CH:3]=[C:2]([NH:1][S:29]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:31])=[O:30])[CH:7]=[CH:6][CH:5]=2)[C:17]2[C:12](=[C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]3=[CH:15][CH:16]=2)[NH:11]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(3-aminophenyl)-1H-benzo[h]quinazolin-2-one (20 mg, 0.07 mmol) in pyridine (3 mL) was added benzenesulfonyl chloride (127 μL, 0.99 mmol), and stirred at 80° C. for 5 hours. After the solution was cooled to room temperature, the solvent was removed under reduced pressure. The residue was diluted with chloroform, washed with a saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, the residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1), to give the titled compound as a yellow amorphous form (5 mg, yield 15%).

Workup

temperatureAfter the solution was cooled to room temperature
customthe solvent was removed under reduced pressure
additionThe residue was diluted with chloroform
washwashed with a saturated aqueous sodium bicarbonate solution
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-84e424c42257476e9b146949df322e8c
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680110B2

Reaction notes

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