N-(4-Formyl-1,3-thiazol-2-YL)acetamide → 4-[2-[2-(Acetylamino)-4-thiazolyl]ethenyl]-2,3-difluorobenzoic acid

HRID 1892483Notes

Reaction equation

HRID 1892483 reaction equation
[CH:1]([C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:11])[CH3:10])[S:6][CH:7]=1)=O.[Br-].[C:13]([C:16]1[CH:41]=[CH:40][C:19]([CH2:20][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:18]([F:42])[C:17]=1[F:43])([OH:15])=[O:14]>>[C:9]([NH:8][C:5]1[S:6][CH:7]=[C:3]([CH:1]=[CH:20][C:19]2[CH:40]=[CH:41][C:16]([C:13]([OH:15])=[O:14])=[C:17]([F:43])[C:18]=2[F:42])[N:4]=1)(=[O:11])[CH3:10]

Participants

3

Reactant 2

HCID 14931749N-(4-Formyl-1,3-thiazol-2-YL)acetamideHCID 86649992HCID 86649992, compound

Product 1

HCID 866499914-[2-[2-(Acetylamino)-4-thiazolyl]ethenyl]-2,3-difluorobenzoic acidYield 76%

Procedure

N-(4-Formyl-1,3-thiazol-2-yl)acetamide (1.071 g, 6.292 mmol) and (4-carboxy-2,3-difluorobenzyl)(triphenyl)phosphoniumbromide (3.227 g, 6.287 mmol) were condensed by a method similar to that of Production Example 4, step 3, to give 4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]vinyl}-2,3-difluorobenzoic acid (1.550 g, 4.778 mmol, yield 76.0%) as a yellow solid.

Workup

  1. customcondensed by a method similar to that of Production Example 4, step 3

Sources & evidence

ORD record
ord-e791fbe25d5144b78268d1926c1f8765
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

Loading…