Hydrochloric Acid → N-(3-(1-(4-amino-3-methoxyphenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-4-chlorobenzyl)cyclopropanecarboxamide

HRID 508786Notes

Reaction equation

HRID 508786 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][NH:7][C:8]([CH:10]2[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[C:15]1[NH:19][C:18](=[O:20])[N:17]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[C:23]([O:30][CH3:31])[CH:22]=2)[N:16]=1.Cl>[Fe].CO>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([N:17]2[C:18](=[O:20])[NH:19][C:15]([C:3]3[CH:4]=[C:5]([CH:13]=[CH:14][C:2]=3[Cl:1])[CH2:6][NH:7][C:8]([CH:10]3[CH2:12][CH2:11]3)=[O:9])=[N:16]2)=[CH:22][C:23]=1[O:30][CH3:31]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136492347HCID 136492347, compound

Product 1

HCID 136612554N-(3-(1-(4-amino-3-methoxyphenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-4-chlorobenzyl)cyclopropanecarboxamideYield 75.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared according to the procedure as described in step-2 Intermediate-28 by using N-(4-chloro-3-(1-(3-methoxy-4-nitrophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzyl)cyclopropanecarboxamide (0.500 g, 1.12 mmol), iron powder (catalytic amount), methanol (20 mL), conc. HCl (5.0 mL) to afford 0.350 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 0.69 (s, 4H), 1.22 (br s, 2H), 1.60 (m, 1H), 3.97 (s, 3H), 4.33 (d, J=5.4 Hz, 2H), 7.45-7.58 (m, 3H), 7.70 (d, J=9.3 Hz, 1H), 7.87 (s, 1H), 8.13 (d, J=9.0 Hz, 1H), 8.71 (m, 1H), 12.30 (br s, 1H); MS (m/z): 414.09 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-a8a9e5e17737423cb84102e18b415a3d
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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