Dichloromethane → 1-(4-Methoxy-phenyl)-3-methyl-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one

HRID 491960

반응식

HRID 491960 반응식
C(O[C:4]([C:6]1[C:14]2[CH2:13][CH2:12][N:11]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][C:22]4=[O:27])=[CH:17][CH:16]=3)[C:10](=[O:28])[C:9]=2[N:8]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[N:7]=1)=O)C.[Li+].[BH4-].C(Cl)Cl.P(Br)(Br)Br>C1COCC1.CC(O)=O.[Zn]>[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([N:8]2[C:9]3[C:10](=[O:28])[N:11]([C:15]4[CH:20]=[CH:19][C:18]([N:21]5[CH2:26][CH2:25][CH2:24][CH2:23][C:22]5=[O:27])=[CH:17][CH:16]=4)[CH2:12][CH2:13][C:14]=3[C:6]([CH3:4])=[N:7]2)=[CH:34][CH:33]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 24614Phosphorus tribromideHCID 4148881Lithium borohydrideHCID 22240488ethyl 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxo-1-piperidinyl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate

생성물 1

HCID 222404521-(4-Methoxy-phenyl)-3-methyl-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one수율 58%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To 1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (0.59 g, 1.2 mmol) in THF (25 mL) was added 2M LiBH4 in THF (0.96 mL, 1.9 mmol) and the reaction was heated to reflux for 2.5 h. To the crude alcohol were added CH2Cl2 (25 mL) and PBr3 (0.14 mL) and the reaction was stirred 24 h. Extraction with CHCl3, washing with water, and drying (Na2SO4) afforded a crude bromo -compound. The bromo-compound was heated in AcOH (15 mL) and activated Zn (0.39 g, 6 mmol) at 120° C. for 24 h. Purification by HPLC and freeze-drying afforded 30 mg (58%) of a white solid; High Resolution Mass Spec (M+H)+ for C25H27N4O3 431.2092.

후처리

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2.5 h
  3. extractionExtraction with CHCl3
  4. washwashing with water
  5. dry with materialdrying (Na2SO4)
  6. customafforded a crude bromo -compound
  7. customPurification by HPLC
  8. customfreeze-drying

출처 및 근거

ORD 기록
ord-c9a2ddffc4f54082828e812595e9b2fe
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531535B2

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