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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
Notes
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Reaction equation

HRID 69113 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-66fabec70f2a458c9ceea7ca1e6ce6b4
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822448B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes