Methanol → Methyl 3-(4-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1467552ノート

反応式

HRID 1467552 の反応式
[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:21]=[CH:20][C:17](C=O)=[CH:16][CH:15]=3)=[O:13])[CH2:8][CH2:7]2)=[O:5])[CH2:3][CH2:2]1.[CH:22](=[N:29]/[C:30]1[CH:38]=[CH:37][CH:36]=C2C=1COC2=O)\[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:40][O-:41].[Na+].[CH3:43]O.[C:45]([O:49][CH2:50]C)(=[O:48])[CH2:46][CH3:47]>>[CH:1]1([C:4]([N:6]2[CH2:7][CH2:8][N:9]([C:12]([C:14]3[CH:15]=[CH:16][C:17]([CH:43]4[C:40](=[O:41])[C:47]5[C:46]([C:45]([O:49][CH3:50])=[O:48])=[CH:36][CH:37]=[CH:38][C:30]=5[NH:29][CH:22]4[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:20][CH:21]=3)=[O:13])[CH2:10][CH2:11]2)=[O:5])[CH2:3][CH2:2]1

参加物

6

反応物 5

HCID 887MethanolHCID 7749Ethyl PropionateHCID 10942334Sodium MethoxideHCID 866390294-(4-(Cyclopropanecarbonyl)piperazine-1-carbonyl)benzaldehydeHCID 178519069HCID 178519069、化合物

生成物 1

HCID 67258433Methyl 3-(4-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate収率 11%

反応条件

温度
0 °C

実験手順

A mixture of compound 4-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)benzaldehyde (429 mg, 1.5 mmol) and (E)-4-(benzylideneamino)isobenzofuran-1(3H)-one ((355.5 mg, 1.5 mmol) in ethyl propionate (12 mL) was cooled to 0° C. Then a solution of sodium methoxide in methanol [sodium (138 mg, 6 mmol) in methanol (12 mL)] was added dropwise. After the addition, the mixture was stirred at 25° C. for 18 hr. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=10:1 to 1:10) to give methyl 3-(4-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (90 mg, yield 11%). LC-MS (ESI) m/z: 538 (M+1)+.

後処理

  1. additionAfter the addition
  2. customThe mixture was quenched with water (10 mL) and solvent
  3. customwas removed in vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate (50 mL×3)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto give crude product
  10. customThe crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=10:1 to 1:10)

出典と根拠

ORDレコード
ord-ce8b53bbc9a74647abb4bbdc0fa8501c
出典データセット
uspto-grants-2015_04
特許番号
US08999987B2

反応ノート

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