Benzenesulfonyl chloride → HCID 86620404, compound

HRID 252729Notes

Reaction equation

HRID 252729 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]=[C:16]([C:18]2[S:22][C:21]([NH:23][C:24](=[O:26])[CH3:25])=[N:20][C:19]=2[CH3:27])[CH:15]=[CH:14][CH:13]=1.CCCC(C)C>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:16]1[CH:15]=[CH:14][CH:13]=[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:17]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 78922-MethylpentaneHCID 86244441HCID 86244441, compound

Product 1

HCID 86620404HCID 86620404, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzenesulfonyl chloride (0.77 mL) was added to a stirred mixture of N-[5-(6-aminopyridin-2-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (249 mg) and pyridine (10 mL) and the reaction mixture was stirred at room temperature for 30 minutes. The resultant mixture was poured into isohexane (400 mL). The supernatant liquid was decanted from a residual gum. A 7M methanolic ammonia solution (20 mL) was added to the residual gum 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 (296 mg); 1H NMR Spectrum: (DMSO-d6) 2.18 (s, 3H), 2.44 (s, 3H), 6.83 (d, 1H), 7.20 (d, 1H), 7.62 (m, 3H), 7.70 (t, 1H), 8.03 (d, 2H), 11.17 (br s, 1H), 12.12 (s, 1H); Mass Spectrum: M+H+ 389.

Workup

  1. customThe supernatant liquid was decanted from a residual gum
  2. additionA 7M methanolic ammonia solution (20 mL) was added to the residual gum
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. customThe resultant mixture was evaporated
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-eeff6f8680884172961a5f9d622c04c2
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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