Ethyl chloroformate → HCID 10393837, compound

HRID 1198672Notes

Reaction equation

[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[S:34](=[O:37])(=[O:36])[NH2:35])=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4].Cl[C:39]([O:41][CH2:42][CH3:43])=[O:40]>>[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[S:34](=[O:37])(=[O:36])[NH:35][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 10928Ethyl chloroformate

HCID 103469025-n-Butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 10393837HCID 10393837, compound

Procedure

The title compound was prepared from 5-n-butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 13, Step C) and ethyl chloroformate, according to the procedure of Example 14. The crude product was flash chromatographed over silica gel (gradient elution using 0.3-5.0% MeOH/CH2Cl2) to afford the desired material as a white solid, mp 79°-81° C.; homogeneous by TLC (5% MeOH/CH2Cl2); mass spectrum (FAB) m/e 603 (M+1)+, 625 (M+Na)+.

Workup

customchromatographed over silica gel (gradient elution using 0.3-5.0% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-b01816c645c848c7998067b3233453e2
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05281614

Reaction notes

Loading…