Trifluoroacetic acid → 4-Chloro-N-cyclopropyl-3-(5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzenesulfonamide

HRID 59504Notes

Reaction equation

HRID 59504 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10]C(OC(C)(C)C)=O)=[CH:5][CH:4]=1.[Cl:20][C:21]1[CH:31]=[CH:30][C:29]([S:32](=[O:38])(=[O:37])[NH:33][CH:34]2[CH2:36][CH2:35]2)=[CH:28][C:22]=1[C:23]([N:25]=[C:26]=[O:27])=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:20][C:21]1[CH:31]=[CH:30][C:29]([S:32]([NH:33][CH:34]2[CH2:36][CH2:35]2)(=[O:38])=[O:37])=[CH:28][C:22]=1[C:23]1[NH:25][C:26](=[O:27])[N:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:19])[F:18])=[CH:4][CH:5]=2)[N:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 90019516tert-Butyl 2-(4-(trifluoromethyl)phenyl)hydrazinecarboxylateHCID 900195252-chloro-5-(N-cyclopropylsulfamoyl)benzoyl isocyanate

Product 1

HCID 1364924364-Chloro-N-cyclopropyl-3-(5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzenesulfonamideYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by following the procedure as described for Example-83 by using tert-butyl 2-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate (Intermediate-53, 0.050 g, 0.18 mmol), 2-chloro-5-(N-cyclopropylsulfamoyl)benzoyl isocyanate (step-4 of Intermediate-40, 0.108 g, 0.36 mmol), DCM (10 mL) and TFA (3 mL) to afford 0.050 g of desired product. 1H NMR (400 MHz, DMSO d6): δ 0.40-0.42 (m, 2H), 0.50-0.54 (m, 2H), 2.17-2.21 (m, 1H), 7.85 (d, J=8.8 Hz, 2H), 7.92-7.98 (m, 2H), 8.15-8.21 (m, 4H), 12.84 (s, 1H); MS (m/z): 457.15 (M+H+).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-ca8df94dc72c4c65a1fd7a22c9e9b5c8
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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