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

HRID 1508872노트

반응식

HRID 1508872 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-b89de6c8223e48aa89f24b1e4a91e16a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221843B2

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