4-(Trifluoromethoxy)benzoic acid → HCID 86711892, compound

HRID 1475198Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[N:9][C:8]([C:12]([NH:14][NH2:15])=[O:13])=[N:7]1.[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=O)=[CH:24][CH:23]=1>O=P(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[N:9][C:8]([C:12]2[O:13][C:26]([C:25]3[CH:29]=[CH:30][C:22]([O:21][C:20]([F:19])([F:31])[F:32])=[CH:23][CH:24]=3)=[N:15][N:14]=2)=[N:7]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-(3-bromobenzyl)-5-methyl-1H-1,2,4-triazole-3-carbohydrazide (682 mg, 2.19 mmol), dissolved in POCl3 (6 mL), 4-(trifluoromethoxy)benzoic acid (453 mg, 2.19 mmol) was added. The reaction was heated to 100° C. for 2.5 h. The solvent was removed under reduced pressure and the crude material was taken up in EtOAc. The organic layer was then washed with NaHCO3 (3×40 mL) and brine (1×40 mL), dried over Na2SO4, filtered, concentrated under reduced pressure and purified on a Biotage pre-packed silica gel column (MeOH:DCM 2% to 40% MeOH) to afford 2-(1-(3-bromobenzyl)-5-methyl-1H-1,2,4-triazol-3-yl)-5-(4-(trifluoromethoxy)phenyl)-1,3,4-oxadiazole (443 mg, 42%). MS (ES+) C19H13BrF3N5O2 requires: 479, 481 found: 480, 482 [M+H]+(1:1).

Workup

customThe solvent was removed under reduced pressure
washThe organic layer was then washed with NaHCO3 (3×40 mL) and brine (1×40 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
custompurified on a Biotage pre-packed silica gel column (MeOH:DCM 2% to 40% MeOH)

Sources & evidence

ORD record: ord-d3def229904f41649998c7052443dc3e
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018380B2

Reaction notes

Loading…