Trifluoroacetic acid → n-(4-Amino-3-methylphenyl) {[(5-chloro(2-thienyl))sulfonyl]amino}-carboxamide

HRID 1828139Notes

Reaction equation

HRID 1828139 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][S:19]([C:22]2[S:23][C:24]([Cl:27])=[CH:25][CH:26]=2)(=[O:21])=[O:20])=[O:17])=[CH:11][C:10]=1[CH3:28])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][S:19]([C:22]2[S:23][C:24]([Cl:27])=[CH:25][CH:26]=2)(=[O:21])=[O:20])=[O:17])=[CH:11][C:10]=1[CH3:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22064442N-(4-[(tert-butoxy)carbonylamino]-3-methylphenyl}{[(5-chloro(2-thienyl))sulfonyl]amino}carboxamide

Product 1

HCID 22064409n-(4-Amino-3-methylphenyl) {[(5-chloro(2-thienyl))sulfonyl]amino}-carboxamideYield 136.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a chilled solution of N-{4-[(tert-butoxy)carbonylamino]-3-methylphenyl}{[(5-chloro(2-thienyl))sulfonyl]amino}carboxamide (0.246 g, 0.55 mmol) in CH2Cl2 (5 mL) was added neat TFA (1.1 mL). The reaction mixture was stirred cold for 1.5 hr, concentrated in vacuo, azeotroped with heptane and dried to give N-(4-amino-3-methylphenyl) {[(5-chloro(2-thienyl))sulfonyl]amino}-carboxamide (0.26 g) as the mono TFA salt. ES-MS (M+H)+=346.

Workup

  1. concentrationconcentrated in vacuo
  2. customazeotroped with heptane
  3. customdried

Sources & evidence

ORD record
ord-da9fe9cdf5784a39881d29965b8f67c3
Source dataset
uspto-grants-2006_06
Patent number
US07056926B2

Reaction notes

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