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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
ノート
印刷プレビュー

反応式

HRID 69113 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-66fabec70f2a458c9ceea7ca1e6ce6b4
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822448B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート