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

HRID 474673Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[N:18]#[C:19][NH2:20].OS(C(F)(F)F)(=O)=O>C1COCC1>[C:19](=[NH:18])([O:17][CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)=[CH:14][CH:13]=1)[NH2:20]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 2-{4-[(6-methyl-2-pyridinyl)oxy]phenyl}ethanol (1.7 g, 7.41 mmol) and cyanamide (0.405 g, 9.64 mmol) in dry THF (20 mL) under nitrogen was added triflic acid (0.856 mL, 9.64 mmol). The mixture was heated at 55° C. for 4 h. Purification via reverse phase flash chromatography afforded the title compound (1.4 g, 3.64 mmol, 49.1% yield) as a colorless oil. LCMS: rt=1.87 min, [M+H+]=272

Workup

customPurification via reverse phase flash chromatography

Sources & evidence

ORD record: ord-d96a2ac225ec4ed4b56db5bd07d15d42
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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