Phosphorus oxychloride → N-(4-Chloro-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-2-yl)acetamide

HRID 1517461노트

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HRID 1517461 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[C:13]([NH:19][C:20](=[O:22])[CH3:21])[NH:14][C:15](=O)[C:16]=3[N:17]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)[Cl:34]>O1CCOCC1>[Cl:34][C:15]1[C:16]2[N:17]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:9]=[CH:10][C:11]=2[N:12]=[C:13]([NH:19][C:20](=[O:22])[CH3:21])[N:14]=1

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 1360008912-acetamido-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidin-4(3H)-one

생성물 1

HCID 57698346N-(4-Chloro-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-2-yl)acetamide수율 52.6%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To a suspension of N-[6-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-pyrido[3,2-d]pyrimidin-2-yl]-acetamide (0.77 g, 2.58 mmol) and DIEA (1.34 mL, 7.74 mmol) in dioxane (25 mL) was added POCl3 (0.73 mL, 7.74 mmol). The mixture was heated to 80° C. for 30 minutes. After the removal of solvent, the residue was dissolved in ethyl acetate (200 mL) and the solution was filtered through a short column with silica gel. The column was additionally washed with ethyl acetate. The filtrate and washings were combined and concentrated. The precipitate formed was isolated by filtration to give the pure title compound as a brown solid (0.43 g, yield 43%) which was characterised as follows: MS (m/z) 317.0 [M+H]+.

후처리

  1. customAfter the removal of solvent
  2. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  3. filtrationthe solution was filtered through a short column with silica gel
  4. washThe column was additionally washed with ethyl acetate
  5. concentrationconcentrated
  6. customThe precipitate formed
  7. customwas isolated by filtration

출처 및 근거

ORD 기록
ord-06f7b2309fec4d1487012e95de5d0852
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232278B2

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