Cyanamide → 2-(4-{[6-(Trifluoromethyl)-3-pyridinyl]oxy}phenyl)ethyl imidocarbamate

HRID 705892Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 2-(4-{[6-(trifluoromethyl)-3-pyridinyl]oxy}phenyl)ethanol (1.95 g, 6.88 mmol) and cyanamide (0.5 g, 11.89 mmol) in dry THF (20 mL) under nitrogen was added triflic acid (1 mL, 11.26 mmol). The mixture was heated at 55° C. for 4 h. Purification via reverse phase flash chromatography afforded the title compound (1.72 g, 3.92 mmol, 57.0% yield) as a white solid. LCMS: rt=2.42 min, [M+H+]=326

Workup

customPurification via reverse phase flash chromatography

Sources & evidence

ORD record: ord-a40bb73b8ddb462aa4752098041c8b10
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

Loading…