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

HRID 907815
ノート
印刷プレビュー

反応式

HRID 907815 の反応式
[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)C=O)=[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]=[C:16]([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:19]=[CH:20][CH:21]=3)=[O:13])[CH2:10][CH2:11]2)=[O:5])[CH2:2][CH2:3]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 887MethanolHCID 7749Ethyl PropionateHCID 10942334Sodium MethoxideHCID 866390323-(4-(Cyclopropanecarbonyl)piperazine-1-carbonyl)benzaldehydeHCID 178519069HCID 178519069、化合物

生成物 1

HCID 67259852Methyl 3-(3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate
収率 12%

反応条件

温度
0 °C

実験手順

A mixture of 3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)benzaldehyde (286 mg, 1 mmol) and (E)-4-(benzylideneamino)isobenzofuran-1(3H)-one (237 mg, 1 mmol) in ethyl propionate (7.5 mL) was cooled to 0° C. Then a solution of sodium methoxide in methanol [sodium (92 mg, 4 mmol) in methanol (7.5 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-(3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (64 mg, yield 12%). 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-4f39dedeec934b3383094b07426b5755
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08012976B2

反応ノート

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