Benzenesulfonyl chloride → HCID 86620410, compound

HRID 252734Notes

Reaction equation

HRID 252734 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][N:13]=1>N1C=CC=CC=1>[CH3:27][C:19]1[N:20]=[C:21]([NH:23][C:24](=[O:26])[CH3:25])[S:22][C:18]=1[C:15]1[CH:16]=[N:17][C:12]([NH:11][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chloride2×HCID 86244445HCID 86244445, compound

Product 1

HCID 86620410HCID 86620410, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzenesulfonyl chloride (0.192 mL) was added to a stirred mixture of N-[5-(2-aminopyrimidin-5-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (195 mg) and pyridine (10 mL) and the reaction mixture was heated to reflux for 18 hours. Additional benzenesulfonyl chloride (0.384 mL) was added and the mixture was heated to reflux for 2 hours. The reaction mixture was evaporated. A 7M methanolic ammonia solution (10 mL) was added to the residue and the mixture was stirred at room temperature for 1 hour. The resultant mixture was evaporated and the residue was purified by preparative HPLC. There was thus obtained the title compound (55 mg); 1H NMR Spectrum: (DMSOd6) 2.13 (s, 3H), 2.27 (s, 3H), 7.61 (m, 3H), 8.02 (m, 2H), 8.60 (s, 2H), 12.00 (br s, 1H), 12.20 (s, 1H); Mass Spectrum: M+H+ 390.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 18 hours
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 2 hours
  5. customThe reaction mixture was evaporated
  6. additionA 7M methanolic ammonia solution (10 mL) was added to the residue
  7. customThe resultant mixture was evaporated
  8. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-e0ca236f1b004420b80760b2ab023c1e
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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