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

HRID 705921ノート

反応式

HRID 705921 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
55 °C

実験手順

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

後処理

  1. customPurification via reverse phase flash chromatography

出典と根拠

ORDレコード
ord-5039022e27ca45b490f9f510ae0b2882
出典データセット
uspto-grants-2015_11
特許番号
US09174968B2

反応ノート

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