Triethylamine → 1-(3-chloro-phenyl)-6-(4-nitro-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

HRID 1241896노트

반응식

HRID 1241896 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][N:9]=[C:10](Cl)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][CH:7]=1.N1([C:23]2[C:24](=[O:38])[N:25]([C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=3)[CH2:26][CH2:27][CH:28]=2)CCOCC1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:14]([O:13][C:11]([C:10]1[C:28]2[CH2:27][CH2:26][N:25]([C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=3)[C:24](=[O:38])[C:23]=2[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:9]=1)=[O:12])[CH3:15]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 580329Acetic acid, chloro[(3-chlorophenyl)hydrazono]-, ethyl esterHCID 219368093-(4-Morpholinyl)-1-(4-nitrophenyl)-5,6-dihydro-2(1H)-pyridinone

생성물 1

HCID 696667991-(3-chloro-phenyl)-6-(4-nitro-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester수율 47.6%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
80 °C

실험 절차

Part A: A 500 mL flask was charged with N-(3-chlorophenyl)-1-(ethoxycarbonyl)-methanehydrazonoyl chloride (3.67 g, 14.1 mmol), 3-morpholin-4-yl-1-(4-nitro-phenyl)-5,6-dihydro-1H-pyridin-2-one (2.14 g, 7.05 mmol), 50 mL of toluene, and triethylamine (3.57 g, 35.3 mmol). The mixture was heated at 80° C. overnight. After cooling to room temperature, the reaction mixture was treated with trifuloroacetic acid (10.1 g) at rt for 5 h. The mixture was concentrated to dryness under reduced pressure. The residue was dissolved in methylene chloride, washed water and brine, and dried with sodium sulfate. The crude product, after evaporation of the solvent, was purified by silica gel chromatography, eluting with 1:2 ethyl acetate/hexane to yield 1-(3-chloro-phenyl)-6-(4-nitro-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (1.48 g). 1H NMR (300 MHz, CDCl3) δ 8.24 (2H, d, J=9.1 Hz), 7.60 (1H, t, J=1.8 Hz), 7.52 (2H, d, J=9.1 Hz), 7.47˜7.36(2H, m), 4.48 (2H, q, J=7.0 Hz), 4.22 (2H, t, J=6.6 Hz), 3.39 (2H, t, J=6.6 Hz), 1.45 (3H, t, J=7.0 Hz) ppm.

후처리

  1. temperatureAfter cooling to room temperature
  2. concentrationThe mixture was concentrated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed water and brine
  5. dry with materialdried with sodium sulfate
  6. customThe crude product, after evaporation of the solvent
  7. customwas purified by silica gel chromatography
  8. washeluting with 1:2 ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-8e53976f725f4bfaa82dd404107f1a9a
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115627B2

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