Tetrahydrofuran → 2-{4-[(3-Fluoro-4-methylphenyl)oxy]phenyl}ethyl imidocarbamate

HRID 705914Notes

Reaction equation

HRID 705914 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[CH:15][CH:14]=2)=N[C:7]=1C(F)(F)F.[N:22]#[C:23][NH2:24].OS([C:29]([F:32])(F)F)(=O)=O.[CH2:33]1COCC1>>[C:23](=[NH:24])([O:21][CH2:20][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][C:5]2[CH:4]=[CH:3][C:2]([CH3:7])=[C:29]([F:32])[CH:33]=2)=[CH:18][CH:17]=1)[NH2:22]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 9864CyanamideHCID 62406Trifluoromethanesulfonic acidHCID 677738582-(4-((5-Chloro-6-(trifluoromethyl)pyridin-2-yl)oxy)phenyl)ethanol

Product 1

HCID 677758982-{4-[(3-Fluoro-4-methylphenyl)oxy]phenyl}ethyl imidocarbamateYield 84%

Conditions

Temperature
55 °C

Procedure

To a solution of 2-(4-((5-chloro-6-(trifluoromethyl)pyridin-2-yl)oxy)phenyl)ethanol (0.2 g, 0.630 mmol) and cyanamide (0.053 g, 1.259 mmol) in dry THF (3 mL) under nitrogen was added triflic acid (0.112 mL, 1.259 mmol). The mixture was heated at 55° C. for 1 h. Purification via reverse phase flash chromatography afforded the title compound (250 mg, 0.529 mmol, 84% yield) as a white solid. LCMS: rt=2.77 min, [M+H+]=360

Workup

  1. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-dcc2a7ac65864f0b84457e29573ec0bf
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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