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

HRID 705912Notes

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-dd35f681a50349ea8869b22684269244
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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