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Cyanamide → 2-(4-{[6-(Trifluoromethyl)-3-pyridinyl]oxy}phenyl)ethyl imidocarbamate

HRID 474653
Notes
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Reaction equation

HRID 474653 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[N:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][OH:18])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[N:21]#[C:22][NH2:23].OS(C(F)(F)F)(=O)=O>C1COCC1>[C:22](=[NH:21])([O:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:6]2[CH:7]=[N:8][C:3]([C:2]([F:19])([F:1])[F:20])=[CH:4][CH:5]=2)=[CH:11][CH:12]=1)[NH2:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 9864CyanamideHCID 62406Trifluoromethanesulfonic acidHCID 677763732-(4-{[6-(Trifluoromethyl)-3-pyridinyl]oxy}phenyl)ethanol

Product 1

HCID 677751812-(4-{[6-(Trifluoromethyl)-3-pyridinyl]oxy}phenyl)ethyl imidocarbamateYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-(4-{[6-(trifluoromethyl)-3-pyridinyl]oxy}phenyl)ethanol (1.95 g, 6.88 mmol) and cyanamide (0.5 g, 11.89 mmol) in dry THF (20 mL) under nitrogen was added triflic acid (1 mL, 11.26 mmol). The mixture was heated at 55° C. for 4 h. Purification via reverse phase flash chromatography afforded the title compound (1.72 g, 3.92 mmol, 57.0% yield) as a white solid. LCMS: rt=2.42 min, [M+H+]=326

Workup

  1. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-62d602a0f92d4629abd06394c9ef7e3c
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637536B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes