Water → 2-(5-(aminomethyl)-2-chloro-4-fluorophenyl)-5-(4-iodophenyl)-2H-1,2,4-triazol-3(4H)-one

HRID 508881Notes

Reaction equation

HRID 508881 reaction equation
[Cl:1][C:2]1[C:15]([N:16]2[C:20](=[O:21])[NH:19][C:18]([C:22]3[CH:27]=[CH:26][C:25]([I:28])=[CH:24][CH:23]=3)=[N:17]2)=[CH:14][C:5]([CH2:6][NH:7]C(=O)C(F)(F)F)=[C:4]([F:29])[CH:3]=1.[OH-].[K+].O>C1COCC1>[NH2:7][CH2:6][C:5]1[C:4]([F:29])=[CH:3][C:2]([Cl:1])=[C:15]([N:16]2[C:20](=[O:21])[NH:19][C:18]([C:22]3[CH:23]=[CH:24][C:25]([I:28])=[CH:26][CH:27]=3)=[N:17]2)[CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 136492435N-(4-chloro-2-fluoro-5-(4,5-dihydro-3-(4-iodophenyl)-5-oxo-1,2,4-triazol-1-yl)benzyl)-2,2,2-trifluoroacetamide

Product 1

HCID 1364924392-(5-(aminomethyl)-2-chloro-4-fluorophenyl)-5-(4-iodophenyl)-2H-1,2,4-triazol-3(4H)-oneYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure described in Intermediate-66 by using N-(4-chloro-2-fluoro-5-(4,5-dihydro-3-(4-iodophenyl)-5-oxo-1,2,4-triazol-1-yl)benzyl)-2,2,2-trifluoroacetamide (0.550 g, 1.01 mmol), KOH (0.285 g, 5.09 mmol), water (5 mL) and THF (15.0 mL) to afford 0.400 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 3.59 (m, 2H), 3.71 (s, 1H), 7.38 (d, J=9.6 Hz, 1H), 7.54 (d, J=7.8 Hz, 1H), 7.60-7.69 (m, 4H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-003ba2522f2a4906b75f71c65c3f0ffb
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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