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 639587ノート

反応式

HRID 639587 の反応式
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

参加物

8

反応物 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

生成物 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-one収率 58%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-77b39c7995164c6ea5c4c07cf3cb2dec
出典データセット
uspto-grants-2010_04
特許番号
US07691846B2

反応ノート

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