Trifluoroacetic acid → 4-Chloro-3-(1-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-N-cyclopropylbenzenesulfonamide

HRID 59505Notes

Reaction equation

HRID 59505 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9]C(OC(C)(C)C)=O)=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:28]=[CH:27][C:26]([S:29](=[O:35])(=[O:34])[NH:30][CH:31]2[CH2:33][CH2:32]2)=[CH:25][C:19]=1[C:20]([N:22]=[C:23]=[O:24])=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:17][C:18]1[CH:28]=[CH:27][C:26]([S:29]([NH:30][CH:31]2[CH2:33][CH2:32]2)(=[O:35])=[O:34])=[CH:25][C:19]=1[C:20]1[NH:22][C:23](=[O:24])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 59485730tert-Butyl 2-(4-chlorophenyl)hydrazinecarboxylateHCID 900195252-chloro-5-(N-cyclopropylsulfamoyl)benzoyl isocyanate

Product 1

HCID 1364923884-Chloro-3-(1-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-N-cyclopropylbenzenesulfonamide

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-chlorophenyl)hydrazinecarboxylate (Intermediate-62, 0.050 g, 0.20 mmol), 2-chloro-5-(N-cyclopropylsulfamoyl)benzoyl isocyanate (step-4 of Intermediate-40, 0.123 g, 0.41 mmol), DCM (10 mL) and TFA (3 mL) to afford 0.025 g, of pure product. 1H NMR (400 MHz, DMSO de): δ 0.39-0.41 (m, 2H), 0.49-0.52 (m, 2H), 2.17-2.20 (m, 1H), 7.52-7.55 (d, J=8.0 Hz, 2H), 7.91-8.00 (m, 5H), 8.14 (m, 1H), 12.60 (br s, 1H); MS (m/z): 425.10 (M+).

Workup

  1. customto afford 0.025 g

Sources & evidence

ORD record
ord-054ba1edb3ba4800be3bb363a31fae49
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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