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

HRID 474687Notes

Reaction equation

HRID 474687 reaction equation
F[C:2]1[CH:3]=[C:4]([CH2:19][CH2:20][OH:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=NC(C(F)(F)F)=N[CH:14]=1.[N:22]#[C:23][NH2:24].OS([C:29]([F:32])(F)F)(=O)=O.[CH2:33]1[CH2:37]OC[CH2:34]1>>[C:23](=[NH:24])([O:21][CH2:20][CH2:19][C:4]1[CH:3]=[CH:2][C:7]([O:8][C:9]2[CH:14]=[CH:34][C:33]([CH3:37])=[C:29]([F:32])[CH:10]=2)=[CH:6][CH:5]=1)[NH2:22]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 9864CyanamideHCID 62406Trifluoromethanesulfonic acidHCID 677742942-(3-Fluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)phenyl)ethanol

Product 1

HCID 677758982-{4-[(3-Fluoro-4-methylphenyl)oxy]phenyl}ethyl imidocarbamateYield 24.95%

Conditions

Temperature
55 °C

Procedure

To a solution of 2-(3-fluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)phenyl)ethanol (756 mg, 1.251 mmol) and cyanamide (105 mg, 2.501 mmol) in dry THF (6 mL) under nitrogen was added triflic acid (0.222 mL, 2.501 mmol). The mixture was heated at 55° C. for 3 h. Purification via reverse phase flash chromatography afforded the title compound (1 g, 2.104 mmol, 24.95% yield). LCMS: rt=2.41 min, [M+H+]=345

Workup

  1. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-b139990d43374fd1a935bb9f2ea38e04
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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