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1,1'-Carbonyldiimidazole → 8-bromo-1-(tetrahydro-2H-pyran-4-yl)-7-(trifluoromethyl)-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one

HRID 69113
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인쇄 미리보기

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HRID 69113 반응식
[Br:1][C:2]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:5]([NH2:6])=[C:4]([C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:16]=[CH:15][CH:14]=2)[CH:3]=1.CCN(C(C)C)C(C)C.C1N=CN([C:38](N2C=NC=C2)=[O:39])C=1.C(OC(C)C)(C)C.C(OCC)(=O)C>CN1CCCC1=O>[Br:1][C:2]1[C:8]([C:9]([F:11])([F:12])[F:10])=[CH:7][C:5]2[NH:6][C:38](=[O:39])[C:14]3[CH:15]=[N:16][N:17]([CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:13]=3[C:4]=2[CH:3]=1
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참가 물질

6

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 22281796Diisopropylether ethyl acetateHCID 866943184-bromo-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]-5-(trifluoromethyl)aniline

생성물 1

HCID 1363368568-bromo-1-(tetrahydro-2H-pyran-4-yl)-7-(trifluoromethyl)-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one수율 85.6%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
150 °C

실험 절차

To a mixture of 3.23 g of 4-bromo-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]-5-(trifluoromethyl)aniline and 32 mL of N-methylpyrrolidone were added 2.6 mL of DIPEA and 1.8 g of CDI, followed by stirring at 150° C. for 1.5 hours. After ice-cooling, diisopropyl ether/ethyl acetate (4/1) and ice were added thereto, followed by stirring. The precipitated solid was collected by filtration, and washed with water and diisopropyl ether/ethyl acetate (4/1). The obtained solid was added to diisopropyl ether/ethyl acetate (4/1), and heated, followed by stirring at room temperature for 10 minutes, and the solid was collected by filtration, washed with diethyl ether, and then dried under reduced pressure to obtain 2.95 g of 8-bromo-1-(tetrahydro-2H-pyran-4-yl)-7-(trifluoromethyl)-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one.

후처리

  1. temperatureAfter ice-cooling
  2. stirringby stirring
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water and diisopropyl ether/ethyl acetate (4/1)
  5. additionThe obtained solid was added to diisopropyl ether/ethyl acetate (4/1)
  6. temperatureheated
  7. stirringby stirring at room temperature for 10 minutes
  8. filtrationthe solid was collected by filtration
  9. washwashed with diethyl ether
  10. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-66fabec70f2a458c9ceea7ca1e6ce6b4
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822448B2

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