Trifluoroacetic acid → 2-(4-{[3-(Trifluoromethyl)phenyl]oxy}phenyl)ethyl imidocarbamate triflate

HRID 474586Notes

Reaction equation

HRID 474586 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=1.[N:21]#[C:22][NH2:23].[OH:24][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26].C(O)(C(F)(F)F)=O>C1COCC1>[OH:27][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:26])=[O:24].[C:22](=[NH:21])([O:15][CH2:14][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([O:6][C:5]2[CH:16]=[CH:17][CH:18]=[C:3]([C:2]([F:19])([F:20])[F:1])[CH:4]=2)=[CH:12][CH:11]=1)[NH2:23]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9864CyanamideHCID 62406Trifluoromethanesulfonic acidHCID 677742022-(4-(3-(Trifluoromethyl)phenoxy)phenyl)ethanol

Product 1

HCID 866661922-(4-{[3-(Trifluoromethyl)phenyl]oxy}phenyl)ethyl imidocarbamate triflateYield 59.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-(4-(3-(trifluoromethyl)phenoxy)phenyl)ethanol (1.395 g, 4.94 mmol) and cyanamide (0.249 g, 5.93 mmol) in THF (15 mL) was added triflic acid (0.527 mL, 5.93 mmol) under argon. The mixture was heated at 55° C. for 3 h. The mixture was purified by a reverse phase biotage with TFA affording the title compound (1.4 g, 59.8% yield). LCMS: rt=1.23 min, [M+H+]=325

Sources & evidence

ORD record
ord-a476340104c446de9dd31ced2149706f
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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