Trifluoroacetic acid → methyl 4-(1-(2,6-dichlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-2-methoxybenzoate

HRID 508813Notes

Reaction equation

HRID 508813 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]([C:18](=[O:34])[NH:19][C:20](=O)[C:21]1[CH:26]=[CH:25][C:24]([C:27]([O:29][CH3:30])=[O:28])=[C:23]([O:31][CH3:32])[CH:22]=1)[NH:10]C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18](=[O:34])[NH:19][C:20]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([O:29][CH3:30])=[O:28])=[C:23]([O:31][CH3:32])[CH:22]=2)=[N:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90065714Tert-butyl 2-(2,6-dichlorophenyl)-2-((3-methoxy-4-(methoxycarbonyl) benzoyl)carbamoyl)hydrazinecarboxylate

Product 1

HCID 136492383methyl 4-(1-(2,6-dichlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-2-methoxybenzoateYield 52.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in step-2 of Intermediate-9 by using tert-butyl 2-(2,6-dichlorophenyl)-2-((3-methoxy-4-(methoxycarbonyl)benzoyl)carbamoyl)hydrazinecarboxylate (1.5 g, 2.9 mmol), DCM (20 mL) and trifluoro acetic acid (2.0 mL) to afford 0.600 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.80 (s, 3H), 3.80 (s, 3H), 7.49-7.71 (m, 3H), 7.74-7.79 (m, 3H), 12.85 (s, 1H); MS (m/z): 393.95 (M)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6f41c520a0d0452197c12f9df9500d6b
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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