Hydrochloric Acid → HCID 71491312, compound

HRID 2368537Notes

Reaction equation

[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:3]=1[CH2:4][S:5][C:6]1[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])[C:8]([OH:11])=[N:9][N:10]=1.[Cl:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:29]=1[CH2:30]Br.C[O-].[Na+].Cl>CN(C=O)C>[Cl:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:29]=1[CH2:30][O:11][C:8]1[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:19])[F:20])[C:6]([S:5][CH2:4][C:3]2[C:22]([F:26])=[CH:23][CH:24]=[CH:25][C:2]=2[Cl:1])=[N:10][N:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-((2-chloro-6-fluorobenzyl)thio)-4-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-ol (50 mg, 0.124 mmol), 2-chloro-6-fluorobenzyl bromide (39 mg, 0.175 mg), and sodium methoxide (18 mg, 0.33 mmol) in anhydrous DMF was stirred at 80° C. for 8 h. The reaction mixture was cooled to room temperature and neutralized to pH 5 with 5N HCl. The solvent was removed in vacuo and the residue was purified by reverse phase HPLC to afford 3-((2-Chloro-6-fluorobenzyl)oxy)-5-((2-chloro-6-fluorobenzyl)thio)-4-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazole (598). 1H NMR (400 MHz, CDCl3) δ: 7.81-7.79 (m, 1H), 7.63-7.60 (m, 2H), 7.33-7.24 (m, 2H), 7.19-7.14 (m, 2H), 7.10-7.04 (m, 2H), 6.90-6.85 (m, 2H), 5.20 (s, 2H), 4.23 (dd, J=13.0, 1.6, 1H), 4.15 (dd, J=13.0, 1.6, 1H). LC-MS ESI m/z; found 546.0 [M+H]+.

Workup

customThe solvent was removed in vacuo
customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-64d3256e76304d8bacd29263eb0720bc
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703776B2

Reaction notes

Loading…