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

HRID 474675Notes

Reaction equation

HRID 474675 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-2f2472fdad554a4d8dfdc785bcf36596
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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