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

HRID 2205325Notes

Reaction equation

HRID 2205325 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[S:10]([NH:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[S:21][CH2:22][C:23]1[N:24]=[C:25]([NH:28]C(=O)OC(C)(C)C)[S:26][CH:27]=1)(=[O:12])=[O:11].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:28][C:25]1[S:26][CH:27]=[C:23]([CH2:22][S:21][C:15]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=2[NH:13][S:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)(=[O:12])=[O:11])[N:24]=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-571770c4202547408197185d654f3000
Source dataset
uspto-grants-2016_06
Patent number
US09371278B2

Reaction notes

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