Cyanamide → HCID 86666196, compound

HRID 474590Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([CH2:16][CH2:17][OH:18])=[CH:11][C:10]=2[F:19])=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].[N:24]#[C:25][NH2:26].[F:27][C:28]([F:34])([F:33])[S:29]([OH:32])(=[O:31])=[O:30]>C1COCC1>[OH:32][S:29]([C:28]([F:34])([F:33])[F:27])(=[O:31])=[O:30].[C:25](=[NH:24])([O:18][CH2:17][CH2:16][C:12]1[CH:13]=[C:14]([F:15])[C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:20]([F:23])([F:22])[F:21])[CH:4]=2)=[C:10]([F:19])[CH:11]=1)[NH2:26]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3,5-difluorophenyl)ethanol (3.1 g, 8.79 mmol) and cyanamide (0.443 g, 10.55 mmol) in anhydrous THF (20 mL) was added trifluoromethanesulfonic acid (1.873 mL, 21.10 mmol) at 0° C. The reaction mixture was stirred at 60° C. for 4 h. Purification via reverse phase Biotage then afforded the title compound as a white solid (1.5 g, 31.3% yield). LCMS: rt=3.64 min, [M+H+]=395

Workup

customPurification via reverse phase Biotage

Sources & evidence

ORD record: ord-a04ecd07462b4f668587632e19aea5ca
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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