Diisopropylethylamine → 7-methyl-8-{[4-(pyridin-3-ylmethyl)piperazin-1-yl]carbonyl}-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one dihydrochloride

HRID 69130

反応式

HRID 69130 の反応式
[CH3:1][C:2]1[C:3]([C:22]([OH:24])=O)=[CH:4][C:5]2[C:6]3[N:15]([CH:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:26]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(=O)([O-])O.[Na+].C(OCC)(=O)C.[ClH:80]>CO.CN(C=O)C>[ClH:80].[ClH:80].[CH3:1][C:2]1[C:3]([C:22]([N:35]2[CH2:36][CH2:37][N:32]([CH2:31][C:27]3[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=3)[CH2:33][CH2:34]2)=[O:24])=[CH:4][C:5]2[C:6]3[N:15]([CH:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1

参加物

9

反応物 6

HCID 81531DiisopropylethylamineHCID 1569751-[(Pyridin-3-yl)methyl]piperazineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21866389Hydrogen chloride-ethyl acetateHCID 1363368547-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-8-carboxylic acid

生成物 1

HCID 1363368587-methyl-8-{[4-(pyridin-3-ylmethyl)piperazin-1-yl]carbonyl}-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one dihydrochloride

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 120 mg of 7-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-8-carboxylic acid and 2.4 mL of DMF were added 130 mg of 1-(pyridin-3-ylmethyl)piperazine, 0.19 mL of DIPEA, and 177 mg of TBTU, followed by stirring at room temperature overnight. The reaction mixture was ice-cooled and poured into a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic 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 (chloroform/methanol=100/0-92/8) to obtain white powder. The powder was suspended in 1 mL of methanol, and 0.37 mL of a 4 M hydrogen chloride-ethyl acetate solution was added thereto, followed by stirring for 30 minutes. The obtained powder was collected by filtration, washed with methanol, and then dried under reduced pressure to obtain 82 mg of 7-methyl-8-{[4-(pyridin-3-ylmethyl)piperazin-1-yl]carbonyl}-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one dihydrochloride as a white solid.

後処理

  1. temperaturecooled
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic 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 (chloroform/methanol=100/0-92/8)
  7. customto obtain white powder
  8. stirringby stirring for 30 minutes
  9. filtrationThe obtained powder was collected by filtration
  10. washwashed with methanol
  11. customdried under reduced pressure

出典と根拠

ORDレコード
ord-eed1a08719ed4f208c9b20c0edd39357
出典データセット
uspto-grants-2014_09
特許番号
US08822448B2

関連ノート

読み込み中…