N,N-Diethylaniline → 4'-{[5-oxo-7-propyl-4-(tetrahydro-2H-pyran-4-yl)-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

HRID 519872노트

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HRID 519872 반응식
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[NH:12][N:11]=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH:28]([C:34](=O)[CH2:35][CH2:36][CH3:37])[C:29](OCC)=[O:30])=[CH:23][CH:22]=1)#[N:14].N12CCCN=C1CCCCC2.C(N(CC)C1C=CC=CC=1)C>Cl>[O:30]=[C:29]1[C:28]([CH2:27][C:24]2[CH:25]=[CH:26][C:21]([C:16]3[C:15]([C:13]#[N:14])=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:22][CH:23]=2)=[C:34]([CH2:35][CH2:36][CH3:37])[N:12]2[N:11]=[CH:10][CH:9]=[C:8]2[N:7]1[CH:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1

참가 물질

6

반응물 4

HCID 7061N,N-DiethylanilineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 67009691N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-amine

생성물 1

HCID 670101954'-{[5-oxo-7-propyl-4-(tetrahydro-2H-pyran-4-yl)-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile수율 88.3%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

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온도
180 °C

실험 절차

A mixture of N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-amine (1.00 g), ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (4.20 g), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.9 mL) and N,N-diethylaniline (10 mL) was stirred at 180° C. overnight, allowed to cool, and poured into 1 M hydrochloric acid (50 mL), and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (2.39 g, 88%).

후처리

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-accddf8530134884ad054b0a2a72b59b
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115136B2

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