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

HRID 705829Notes

Reaction equation

HRID 705829 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-067f62e8ea9e4d61b0cf9f1fa1c35401
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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