Dimethyl Sulfoxide → HCID 72343932, compound

HRID 2369050Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([C:28](=[N:30][OH:31])[CH3:29])=[N:9]1.[OH-].[K+].Cl.[CH3:35][N:36]([CH3:40])[CH2:37][CH2:38]Cl.CS(C)=O>O>[CH3:35][N:36]([CH3:40])[CH2:37][CH2:38][O:31][N:30]=[C:28]([C:10]1[CH:11]=[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=3)=[CH:16][CH:17]=2)[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:9]=1)[CH3:29]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-[1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]ethanone oxime (196 mg, 0.415 mmol), KOH (142 mg, 2.3 mmol), 2-(dimethylamino)ethyl chloride hydrochloride (185 mg, 1.3 mmol), and anhydrous DMSO (5 mL) was stirred at 60° C. in a sealed vial for 3 h. The reaction mixture was diluted with water, extracted with ether. The combined extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by flash chromatography (0-30% MeOH/DCM) to give the title compound as a white solid (50 mg, 22%). 1HNMR (CDCl3): δ8.04 (d, 1H), 7.83-7.81 (m, 1H), 7.74-7.71 (m, 1H), 7.57-7.43 (m, 5H), 7.21 (d, 1H), 7.00 (s, 1H), 6.76 (d, 1H), 4.38 (t, 2H), 3.07 9s, 3H), 2.78 (m, 2H), 2.40 (brs, 6H), 2.31 (s, 3H).

Workup

extractionextracted with ether
washThe combined extracts were washed with brine
dry with materialdried over Na2SO4
customevaporated in vacuo
customThe residue was purified by flash chromatography (0-30% MeOH/DCM)

Sources & evidence

ORD record: ord-be129e70b6c0488eaca6318bf9c94c60
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703805B2

Reaction notes

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