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Cesium fluoride → N-[4-Methyl-5-(6-phenylsulfonylaminopyrazin-2-yl)-1,3-thiazol-2-yl]acetamide

HRID 252736
Notes
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Reaction equation

HRID 252736 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].Cl[C:12]1[N:17]=[C:16]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:15]=[N:14][CH:13]=1.[F-].[Cs+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CS(C)=O>[CH3:10][C:8]1[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=1[C:12]1[CH:13]=[N:14][CH:15]=[C:16]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[N:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 25953Cesium fluorideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2809072-Acetamido-4-methylthiazoleHCID 86244447N-(6-chloropyrazin-2-yl)benzenesulfonamide

Product 1

HCID 86620413N-[4-Methyl-5-(6-phenylsulfonylaminopyrazin-2-yl)-1,3-thiazol-2-yl]acetamideYield 4.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-acetamido-4-methylthiazole (891 mg), N-(6-chloropyrazin-2-yl)benzenesulfonamide (1.4 g), palladium acetate (94 mg), caesium fluoride (2.35 g), tri-tert-butylphosphine (0.34M in hexane, 2.4 mL) and DMSO (45 mL) was purged with nitrogen. The resultant mixture was stirred and heated to 160° C. for 3.5 hours. The bulk of the DMSO was evaporated and water (50 mL) was added. The resultant solid was filtered off, washed with water and dried under vacuum. A 19:1 mixture of dichloromethane and methanol was added and the mixture was filtered. The filtrate was evaporated and the residue was purified by column chromatography on silica using a solvent gradient of 3% to 5% methanol in dichloromethane as eluent. There was thus obtained the title compound as a solid (95 mg); 1H NMR Spectrum: (DMSOd6) 2.20 (s, 3H), 2.49 (s, 3H), 7.60-7.70 (m, 3H), 8.06 (m, 2H), 8.11 (s, 1H), 8.47 (s, 1H), 11.68 (s, 1H), 12.27 (s, 1H); Mass Spectrum: M+H+ 390.

Workup

  1. customwas purged with nitrogen
  2. customThe bulk of the DMSO was evaporated
  3. additionwater (50 mL) was added
  4. filtrationThe resultant solid was filtered off
  5. washwashed with water
  6. customdried under vacuum
  7. additionA 19:1 mixture of dichloromethane and methanol
  8. additionwas added
  9. filtrationthe mixture was filtered
  10. customThe filtrate was evaporated
  11. customthe residue was purified by column chromatography on silica using a solvent gradient of 3% to 5% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-c7cf4d00806a4f0e918d43a1c9bfb52b
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07868188B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes