Benzenesulfonamide → HCID 86620417, compound

HRID 252740Notes

Reaction equation

Cl[C:2]1[N:7]=[N:6][CH:5]=[C:4]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:16])[CH3:15])=[N:10][C:9]=2[CH3:17])[CH:3]=1.[C:18]1([S:24]([NH2:27])(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O>[CH3:17][C:9]1[N:10]=[C:11]([NH:13][C:14](=[O:16])[CH3:15])[S:12][C:8]=1[C:4]1[CH:3]=[C:2]([NH:27][S:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:26])=[O:25])[N:7]=[N:6][CH:5]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of N-[5-(6-chloropyridazin-4-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (55 mg), benzenesulphonamide (49 mg), caesium carbonate (101 mg), cuprous iodide (30 mg) and DMA (1.5 mL) was heated in a microwave reactor to 200° C. under an argon atmosphere for 3 hours. The resultant mixture was evaporated and the residue was purified by preparative HPLC on reversed phase silica using a solvent gradient of 10% to 100% acetonitrile in water (containing 1% acetic acid) as eluent. The material so obtained was triturated under diethyl ether. There was thus obtained the title compound as a solid (7.3 mg); 1H NMR Spectrum: (DMSOd6+CD3CO2D) 2.20 (s, 3H), 2.43 (s, 3H), 7.51-7.64 (m, 3H), 7.75 (s, 1H), 7.89 (d, 2H), 8.51 (s, 1H); Mass Spectrum: M+H+ 390.

Workup

customThe resultant mixture was evaporated
customthe residue was purified by preparative HPLC on reversed phase silica using a solvent gradient of 10% to 100% acetonitrile in water (containing 1% acetic acid) as eluent
customThe material so obtained
customwas triturated under diethyl ether

Sources & evidence

ORD record: ord-66a61e56b6884bbcaa51cb7a692f5c95
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868188B2

Reaction notes

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