HCID 136492378, compound → HCID 136492453, compound

HRID 508784Notes

Reaction equation

HRID 508784 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][NH:7]C(=O)C(F)(F)F)=[CH:4][C:3]=1[C:16]1[NH:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[C:24]([O:31][CH3:32])[CH:23]=2)[N:17]=1>[OH-].[K+]>[NH2:7][CH2:6][C:5]1[CH:14]=[CH:15][C:2]([Cl:1])=[C:3]([C:16]2[NH:20][C:19](=[O:21])[N:18]([C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[C:24]([O:31][CH3:32])[CH:23]=3)[N:17]=2)[CH:4]=1

Participants

3

Reactant 1

HCID 136492378HCID 136492378, compound

Product 1

HCID 136492453HCID 136492453, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

The solution of N-(4-chloro-3-(1-(3-methoxy-4-nitrophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzyl)-2,2,2-trifluoroacetamide (0.500 g, 1.06 mmol) in 20% aq. KOH (20 mL) was stirred for 2-3 h at RT. Excess of solvent was removed under vacuum and filtered off remaining reaction mass to afford 0.400 g of desired product. 1H NMR (300 MHz, DMSO d6): δ1.80 (br s, 2H), 3.72 (s, 2H), 3.91 (s, 3H), 7.27-7.39 (m, 2H), 7.78 (d, J=9.9 Hz, 2H), 8.98 (d, J=8.7 Hz, 1H), 8.25 (s, 1H); MS (m/z): 375.91 (M)+.

Workup

  1. customExcess of solvent was removed under vacuum
  2. filtrationfiltered off
  3. customreaction mass

Sources & evidence

ORD record
ord-5b1e94b10d5f40c1a13799819df5b74e
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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