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

HRID 474683노트

반응식

HRID 474683 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH2:19][CH2:20][OH:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]=1.[N:22]#[C:23][NH2:24].OS(C(F)(F)F)(=O)=O>C1COCC1>[C:23](=[NH:22])([O:21][CH2:20][CH2:19][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[N:10]=2)=[C:2]([F:1])[CH:3]=1)[NH2:24]

참가 물질

5

반응물 3

HCID 9864CyanamideHCID 62406Trifluoromethanesulfonic acidHCID 668254582-(3-Fluoro-4-((6-(trifluoromethyl)pyridin-2-yl)oxy)phenyl)ethanol

생성물 1

HCID 677746472-(3-Fluoro-4-{[6-(trifluoromethyl)-2-pyridinyl]oxy}phenyl)ethyl imidocarbamate수율 44%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
55 °C

실험 절차

To a solution of 2-(3-fluoro-4-{[6-(trifluoromethyl)-2-pyridinyl]oxy}phenyl)ethanol (70 mg, 0.232 mmol) and cyanamide (11.72 mg, 0.279 mmol) in THF (5 mL) was added triflic acid (0.025 mL, 0.279 mmol) under argon. The mixture was heated at 55° C. for 3 h. Purification via reverse phase flash chromatography then afforded the title compound (50 mg, 0.102 mmol, 43.7% yield). LCMS: rt=2.53 min, [M+H+]=344

후처리

  1. customPurification via reverse phase flash chromatography

출처 및 근거

ORD 기록
ord-39c4706cd7054cdf9f7d2aaa86894334
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637536B2

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