Pyridine → HCID 86620412, compound

HRID 252735Notes

Reaction equation

HRID 252735 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N[C:12]1[N:13]=[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])=[N:16][CH:17]=1.[N:28]1C=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([NH:28][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:14]=[N:13][CH:12]=[CH:17][NH:16]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chloride2×HCID 86244446HCID 86244446, compound

Product 1

HCID 86620412HCID 86620412, compound

Conditions

Temperature
85 °C

Procedure

Benzenesulfonyl chloride (0.115 mL) was added to a stirred mixture of N-[5-(5-aminopyrazin-2-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (75 mg) and pyridine (5 mL) and the reaction mixture was heated to 85° C. for 2 hours. Additional benzenesulfonyl chloride (0.115 mL) was added and the mixture was heated to reflux for 10 minutes. 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 (22 mg); 1H NMR Spectrum: (DMSOd6) 2.12 (s, 3H), 2.46 (s, 3H), 7.58 (m, 3H), 7.92 (m, 2H), 8.31 (s, 1H), 8.41 (s, 1H), 11.56, (br s, 1H), 12.11 (s, 1H); Mass Spectrum: M+H+ 390.

Workup

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

Sources & evidence

ORD record
ord-6ef562a04ccb4b828c37ea49e0b9a598
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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