Methanol → HCID 66918942、化合物

HRID 2354219ノート

反応式

HRID 2354219 の反応式
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

参加物

5

反応物 2

HCID 887MethanolHCID 66919002HCID 66919002、化合物

生成物 1

HCID 66918942HCID 66918942、化合物

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c6497086923f421d84aa958aa72d6b67
出典データセット
uspto-grants-2010_07
特許番号
US07750154B2

反応ノート

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