Methanol → HCID 66918942, 화합물

HRID 2354219노트

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HRID 2354219 반응식
Cl.[CH:2]1([NH:5][C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH3:33])=[C:12]([NH:14][C:15](=[O:32])[C:16]3[CH:21]=[C:20]([O:22][CH2:23][C@@H:24]4[CH2:28][CH2:27][CH2:26][NH:25]4)[CH:19]=[CH:18][C:17]=3[N+:29]([O-])=O)[CH:13]=2)=[O:7])[CH2:4][CH2:3]1.[CH3:34]O>[Pd].C(O)C>[CH:2]1([NH:5][C:6](=[O:7])[C:8]2[CH:9]=[CH:10][C:11]([CH3:33])=[C:12]([N:14]3[C:15](=[O:32])[C:16]4[C:17](=[CH:18][CH:19]=[C:20]([O:22][CH2:23][C@@H:24]5[CH2:28][CH2:27][CH2:26][NH:25]5)[CH:21]=4)[N:29]=[CH:34]3)[CH:13]=2)[CH2:4][CH2:3]1

참가 물질

5

반응물 2

HCID 887MethanolHCID 66919002HCID 66919002, 화합물

생성물 1

HCID 66918942HCID 66918942, 화합물

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

N-{5-[(Cyclopropylamino)carbonyl]-2-methylphenyl}-2-nitro-5-[(2S)-pyrrolidin-2-ylmethoxy]benzamide hydrochloride salt (2.05 g) and 10% palladium on carbon (0.2 g) were stirred in ethanol (40 ml) and methanol (20 ml) under an atmosphere of hydrogen gas for 19 hours at room temperature. The catalyst was removed by filtration through diatomaceous earth (Celite®) and the filtrate was concentrated. The residue was dissolved in ethanol (40 ml) and stirred with triethylorthoformate (2.16 ml) and glacial acetic acid (0.124 ml) at 80° C. for 3 hours and then concentrated. The residue was diluted with ethyl acetate and washed with saturated aqueous NaHCO3 solution, brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica column eluting with 20% methanol/ethyl acetate followed by 20% methanol/ethyl acetate+1% aqueous ammonia solution to give N-cyclopropyl-4-methyl-3-[4-oxo-6-[(2S)-pyrrolidin-2-ylmethoxy]quinazolin-3(4H)-yl]benzamide (AZ12299441) (0.837 g) as a cream coloured foam solid; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.70 (m, 2H), 1.49 (m, 1H), 1.61-1.76 (m, 2H), 1.85 (m, 1H), 2.15 (s, 3H), 2.85 (m, 3H), 3.42 (m, 1H), 3.95 (d, 2H), 7.52 (m, 2H), 7.58 (s, 1H), 7.73 (d, 1H), 7.84 (s, 1H), 7.91 (d, 1H), 8.19 (s, 1H), 8.42 (d, 1H); Mass Spectrum: M+H+ 419.

후처리

  1. customThe catalyst was removed by filtration through diatomaceous earth (Celite®)
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethanol (40 ml)
  4. concentrationconcentrated
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with saturated aqueous NaHCO3 solution, brine
  7. dry with materialdried (magnesium sulfate)
  8. concentrationconcentrated
  9. customPurification by column chromatography on a silica column
  10. washeluting with 20% methanol/ethyl acetate

출처 및 근거

ORD 기록
ord-c6497086923f421d84aa958aa72d6b67
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07750154B2

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