2-Aminothiazole → HCID 59466004, compound

HRID 1876731Notes

Reaction equation

HRID 1876731 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:15](Cl)(=[O:17])=[O:16])[CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11].[NH2:19][C:20]1[S:21][CH:22]=[CH:23][N:24]=1>N1C=CC=CC=1>[F:11][C:10]([F:13])([F:12])[C:9]([NH:8][C:7]1[CH:6]=[CH:5][C:4]([S:15](=[O:17])(=[O:16])[NH:19][C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[CH:3][C:2]=1[F:1])=[O:14]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 59466125HCID 59466125, compound

Product 1

HCID 59466004HCID 59466004, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Synthesized according to general procedure 70. Under an N2 atmosphere, a mixture of the 3-fluoro-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (5.0 g, 16.4 mmol) and 2-aminothiazole (1.64 g, 16.4 mmol), and pyridine (9.6 mL) was stirred at RT for 19 h. Purification via silica gel chromatography using 0-10% MeOH in CH2Cl2 gave 2,2,2-trifluoro-N-(2-fluoro-4-(N-thiazol-2-ylsulfamoyl)phenyl)acetamide (3.28 g, 54%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=370.1; tR=1.07 min.

Workup

  1. customSynthesized
  2. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-4d744ba596a24e2a83df8e4fb6efcaa7
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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