Sulfuric Acid → 2-(6-((2-(3-Chlorophenyl)-6-ethylpyrimidin-4-yl)oxy)pyridin-3-yl)acetamide

HRID 1508872ノート

反応式

HRID 1508872 の反応式
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[N:18]=[C:17]([O:19][C:20]3[N:25]=[CH:24][C:23]([CH2:26][C:27]#[N:28])=[CH:22][CH:21]=3)[CH:16]=[C:15]([CH2:29][CH3:30])[N:14]=2)[CH:10]=[CH:11][CH:12]=1>C(=O)(O)[O-].[Na+]>[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[N:18]=[C:17]([O:19][C:20]3[N:25]=[CH:24][C:23]([CH2:26][C:27]([NH2:28])=[O:2])=[CH:22][CH:21]=3)[CH:16]=[C:15]([CH2:29][CH3:30])[N:14]=2)[CH:10]=[CH:11][CH:12]=1

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 901111232-(6-((2-(3-Chlorophenyl)-6-ethylpyrimidin-4-yl)oxy)pyridin-3-yl)acetonitrile

生成物 1

HCID 901093772-(6-((2-(3-Chlorophenyl)-6-ethylpyrimidin-4-yl)oxy)pyridin-3-yl)acetamide収率 34%

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

実験手順

Sulfuric acid (2 mL) was added to 2-(6-((2-(3-chlorophenyl)-6-ethylpyrimidin-4-yl)oxy)pyridin-3-yl)acetonitrile (0.061 g, 0.18 mmol) at 0° C. and slowly warmed to rt. The mixture was stirred for 2 h, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the title compound (0.020 g, 34%) as a white solid. MW=368.22. 1H NMR (DMSO-d6, 300 MHz) δ 8.44-8.37 (m, 2H), 8.10-8.05 (m, 1H), 7.92 (s, 1H), 7.70-7.56 (m, 2H), 7.53-7.43 (m, 2H), 7.01 (s, 1H), 6.55 (d, J=9.4 Hz, 1H), 3.30 (d, 2H), 2.93 (q, J=7.6 Hz, 2H), 1.33 (t, J=7.6 Hz, 3H); APCI MS m/z 369 [M+H]+.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

出典と根拠

ORDレコード
ord-b89de6c8223e48aa89f24b1e4a91e16a
出典データセット
uspto-grants-2015_12
特許番号
US09221843B2

反応ノート

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