Benzenesulfonyl chloride, 3,4-dichloro- → 3,4-Dichloro-N-[5-chloro-2-(2,4-dimethyl-pyridine-3-carbonyl)-pyridin-3-yl]-benzenesulfonamide

HRID 1438545Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:9]([C:11]2[C:12]([CH3:18])=[N:13][CH:14]=[CH:15][C:16]=2[CH3:17])=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.CN(C1C=CC=CN=1)C.[Cl:28][C:29]1[CH:30]=[C:31]([S:36](Cl)(=[O:38])=[O:37])[CH:32]=[CH:33][C:34]=1[Cl:35]>N1C=CC=CC=1>[Cl:28][C:29]1[CH:30]=[C:31]([S:36]([NH:1][C:2]2[C:3]([C:9]([C:11]3[C:12]([CH3:18])=[N:13][CH:14]=[CH:15][C:16]=3[CH3:17])=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=2)(=[O:37])=[O:38])[CH:32]=[CH:33][C:34]=1[Cl:35]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (3-Amino-5-chloro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanone (43 mg, 0.16 mmol) and 10 mg of dimethylaminopyridine in 1.0 ml of pyridine was added 3,4-dichlorobenzenesulfonylchloride (70 mg, 0.28 mmol). The mixture was stirred at 80° C. for 3 hours, cooled to room temperature and concentrated. The residue was directly purified by flash column (50% ethyl acetate in hexane) or preparative HPLC (20-80% acetonitrile in water) to afford 18 mg of title compound as an off-white solid. MS: (M+H)/z =470.4.

Workup

temperaturecooled to room temperature
concentrationconcentrated
customThe residue was directly purified by flash column (50% ethyl acetate in hexane) or preparative HPLC (20-80% acetonitrile in water)

Sources & evidence

ORD record: ord-967acbcc40034504bbe5764699a5d7f8
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622583B2

Reaction notes

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