Trifluoroacetic acid → N-(2-{[(2-amino-1,3-thiazol-4-yl)methyl]thio}-5-chlorophenyl)-1-benzofuran-2-sulfonamide

HRID 1631211Notes

Reaction equation

HRID 1631211 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][S:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[NH:22][S:23]([C:26]2[O:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[CH:30]=2)(=[O:25])=[O:24])[N:12]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][S:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[NH:22][S:23]([C:26]2[O:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[CH:30]=2)(=[O:25])=[O:24])[N:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86667123Tert-butyl{4-[({2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorophenyl}thio)methyl]-1,3-thiazol-2-yl}carbamate

Product 1

HCID 86667122N-(2-{[(2-amino-1,3-thiazol-4-yl)methyl]thio}-5-chlorophenyl)-1-benzofuran-2-sulfonamideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl{4-[({2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorophenyl}thio)methyl]-1,3-thiazol-2-yl}carbamate Compound 11 (62 mg, 0.11 mmol), TFA (0.2 ml) in CH2Cl2 (1 ml) was stirred overnight. The solvent was removed in vacuo and the crude product was purified by column chromatography on silica gel (50% ethyl acetate in hexane) to afford the title compound (45 mg, 88%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude product was purified by column chromatography on silica gel (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7cc4827fc1be4e209b4cd046323cedd9
Source dataset
uspto-grants-2014_07
Patent number
US08791161B2

Reaction notes

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