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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
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HRID 907815 반응식
[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
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참가 물질

6

반응물 5

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

생성물 1

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

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온도
0 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-4f39dedeec934b3383094b07426b5755
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08012976B2

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