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Hydrochloric Acid → 3-Cyclopropyl-3-(6-((5-((5,5-dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methoxy)pyrimidin-4-yl)propanoic acid

HRID 709804
ノート
印刷プレビュー

反応式

HRID 709804 の反応式
[CH3:1][C:2]1([CH3:26])[O:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH2:24][OH:25])[CH:12]=[N:13][C:14]=2[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[F:23])[CH2:3]1.Cl[C:28]1[N:33]=[CH:32][N:31]=[C:30]([CH:34]([CH:41]2[CH2:43][CH2:42]2)[CH2:35][C:36]([O:38]CC)=[O:37])[CH:29]=1.[H-].[Na+].Cl>C1COCC1>[CH:41]1([CH:34]([C:30]2[CH:29]=[C:28]([O:25][CH2:24][C:11]3[CH:12]=[N:13][C:14]([C:15]4[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=4[F:23])=[C:9]([O:8][CH2:7][CH:4]4[CH2:3][C:2]([CH3:26])([CH3:1])[O:6][CH2:5]4)[CH:10]=3)[N:33]=[CH:32][N:31]=2)[CH2:35][C:36]([OH:38])=[O:37])[CH2:43][CH2:42]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 117760030Ethyl 3-(6-chloropyrimidin-4-yl)-3-cyclopropylpropanoateHCID 117760261(5-((5,5-Dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methanol

生成物 1

HCID 1177602663-Cyclopropyl-3-(6-((5-((5,5-dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methoxy)pyrimidin-4-yl)propanoic acid
収率 14.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of (5-((5,5-dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methanol (180 mg) and ethyl 3-(6-chloropyrimidin-4-yl)-3-cyclopropylpropanoate (140 mg) in THF (5.0 mL) was slowly added 60% sodium hydride (60 mg) at 0° C. by small portions, and the mixture was stirred at 50° C. for 3 hr. The mixture was acidified with 1N hydrochloric acid at 0° C. and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by preparative HPLC (C18, mobile phase: water/acetonitrile (10 mM NH4HCO3-containing system)), and the obtained fraction was evaporated under reduced pressure to give the title compound (40 mg) as a white solid.

後処理

  1. customat 0° C.
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by preparative HPLC (C18, mobile phase: water/acetonitrile (10 mM NH4HCO3-containing system))
  6. customthe obtained fraction was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-4bd717bda2a246b8b4a11decca86be36
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181186B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート