Benzenesulfonyl chloride → HCID 86620390, compound

HRID 252713Notes

Reaction equation

HRID 252713 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[N:17]=[CH:16][C:15]([C:18]2[S:22][C:21]([NH:23][C:24](=[O:26])[CH3:25])=[N:20][C:19]=2[CH3:27])=[CH:14][C:13]=1[Cl:28]>N1C=CC=CC=1>[Cl:28][C:13]1[CH:14]=[C:15]([C:18]2[S:22][C:21]([NH:23][C:24](=[O:26])[CH3:25])=[N:20][C:19]=2[CH3:27])[CH:16]=[N:17][C:12]=1[NH:11][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 86244435HCID 86244435, compound

Product 1

HCID 86620390HCID 86620390, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Phenylsulfonyl chloride (0.108 mL) was added to a stirred solution of N-[5-(6-amino-5-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (80 mg) in pyridine (1 mL) and the resultant solution was heated to 50° C. for 4 hours. The mixture was cooled to room temperature and concentrated by evaporation. The residue was purified by column chromatography on silica using increasingly polar mixtures of dichloromethane and methanol as eluent. The material so obtained was triturated under diethyl ether. There was thus obtained the title compound as a white solid (38 mg); 1H NMR Spectrum: (DMSOd6) 2.13 (s, 3H), 2.29 (s, 3H), 7.60 (m, 2H), 7.75 (m, 1H), 7.98 (s, 1H), 8.02 (d, 2H), 8.18 (br s, 1H), 10.95 (br s, 1H); Mass Spectrum: M+H+ 423.

Workup

  1. concentrationconcentrated by evaporation
  2. customThe residue was purified by column chromatography on silica using
  3. temperatureincreasingly polar mixtures of dichloromethane and methanol as eluent
  4. customThe material so obtained
  5. customwas triturated under diethyl ether

Sources & evidence

ORD record
ord-7a4ecadb4cd0443a862ef155454d7cae
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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