Cyanamide → 2-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-3-fluorophenyl)ethyl imidocarbamate

HRID 705836Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][C:10]=2[F:18])=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].[N:23]#[C:24][NH2:25].FC(F)(F)S(O)(=O)=O>C1COCC1>[C:24](=[NH:23])([O:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:19]([F:22])([F:20])[F:21])[CH:4]=2)=[C:10]([F:18])[CH:11]=1)[NH2:25]

Participants

Conditions

Temperature: 60 °C

Procedure

To the solution of 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3-fluorophenyl)ethanol (4.0 g, 11.95 mmol) and cyanamide (0.603 g, 14.34 mmol) in anhydrous THF (25 mL) was added trifluoromethanesulfonic acid (2.55 mL, 28.7 mmol) at 0° C. The reaction mixture was stirred at 60° C. for 4 h. Purification via a reverse phase Biotage then afforded the title compound as a white solid (1.5 g, 23.82% yield). LCMS: rt=3.68 min, [M+H+]=377

Workup

customPurification via a reverse phase Biotage

Sources & evidence

ORD record: ord-a09f00d020614000a6ac6a8eb85caa18
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

Loading…