Methanol → 4-(4-Bromo-2-fluorobenzyl)-5-n-butyl-2-[5-(N-n-butylcarbamoyl)-2-chloro-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 36285Notes

Reaction equation

HRID 36285 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:11]([CH2:12][CH2:13][CH2:14][CH3:15])=[N:10][N:9]([C:16]3[CH:21]=[C:20]([C:22]([O:24]C)=O)[CH:19]=[CH:18][C:17]=3[Cl:26])[C:8]2=[O:27])=[C:4]([F:30])[CH:3]=1.C(Cl)Cl.CO>C(N)CCC>[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:11]([CH2:12][CH2:13][CH2:14][CH3:15])=[N:10][N:9]([C:16]3[CH:21]=[C:20]([C:22](=[O:24])[NH:7][CH2:6][CH2:5][CH2:4][CH3:3])[CH:19]=[CH:18][C:17]=3[Cl:26])[C:8]2=[O:27])=[C:4]([F:30])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 100060494-(4-Bromo-2-fluorobenzyl)-5-n-butyl-2-[2-chloro-5-(methoxycarbonyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 100758994-(4-Bromo-2-fluorobenzyl)-5-n-butyl-2-[5-(N-n-butylcarbamoyl)-2-chloro-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Procedure

A solution of 50 mg (0.10 mmole) of 4-(4-bromo-2-fluorobenzyl)-5-n-butyl-2-[2-chloro-5-(methoxycarbonyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step D) in 1 mL of n-butylamine was stirred overnight at 65° C. and then evaporated in vacuo. The residue was flash chromatographed on 15 cc of silica gel (gradient elution with 1-5% MeOH in CH2Cl2) to yield 41 mg (76%) of colorless, glassy solid, mp 114°-116° C.; homogeneous by TLC (95:5 CH2Cl2 --MeOH); mass spectrum (FAB) m/e 537, 539 (M+1)+.

Workup

  1. customevaporated in vacuo
  2. customchromatographed on 15 cc of silica gel (gradient elution with 1-5% MeOH in CH2Cl2)
  3. customto yield 41 mg (76%) of colorless, glassy solid, mp 114°-116° C.

Sources & evidence

ORD record
ord-13a1d66d2bc44ad79cdcc8c9f7bcb438
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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