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

HRID 705825Notes

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][CH:10]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].[N:22]#[C:23][NH2:24].[F:25][C:26]([F:32])([F:31])[S:27]([OH:30])(=[O:29])=[O:28]>C1COCC1>[OH:30][S:27]([C:26]([F:32])([F:31])[F:25])(=[O:29])=[O:28].[C:23](=[NH:22])([O:17][CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:18]([F:19])([F:20])[F:21])[CH:4]=2)=[CH:14][CH:13]=1)[NH2:24]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethanol (2.63 g, 8.30 mmol) and cyanamide (0.419 g, 9.97 mmol) in dry THF (25 mL) under argon was added trifluoromethanesulfonic acid (0.885 mL, 9.97 mmol). The mixture was heated to 55° C. for 3 hrs. Purification via a reverse phase biotage with TFA then afforded the title compound (2.65 g, 62.8% yield). LCMS: rt=2.906 min, [M+H+]=359

Workup

customPurification via a reverse phase biotage with TFA

Sources & evidence

ORD record: ord-5c2ce5e1a9004f2792cd8c59368454e4
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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