Cyclohexylamine → [8-(cyclohexylamino)-1-methyl-1H-pyrazolo[4,3-h]quinazolin-3-yl](phenyl)methanone

HRID 875125Notes

Reaction equation

HRID 875125 reaction equation
C(S([C:11]1[N:20]=[CH:19][C:18]2[CH2:17][CH2:16][C:15]3[C:21]([C:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:26])=[N:22][N:23]([CH3:24])[C:14]=3[C:13]=2[N:12]=1)(=O)=O)C1C=CC=CC=1.[CH:33]1([NH2:39])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>CS(C)=O>[CH:33]1([NH:39][C:11]2[N:20]=[CH:19][C:18]3[CH2:17][CH2:16][C:15]4[C:21]([C:25]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[O:26])=[N:22][N:23]([CH3:24])[C:14]=4[C:13]=3[N:12]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.[CH:33]1([NH:39][C:11]2[N:20]=[CH:19][C:18]3[CH:17]=[CH:16][C:15]4[C:21]([C:25]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[O:26])=[N:22][N:23]([CH3:24])[C:14]=4[C:13]=3[N:12]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

5

Reactant 2

HCID 7965CyclohexylamineHCID 57531727HCID 57531727, compound

Product 2

HCID 57444109HCID 57444109, compoundHCID 57444110[8-(cyclohexylamino)-1-methyl-1H-pyrazolo[4,3-h]quinazolin-3-yl](phenyl)methanoneYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

83 mg (0.19 mmol) of [8-(benzylsulfonyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazolin-3-yl](phenyl)methanone were dissolved in 3 mL of dimethylsulfoxide and cyclohexylamine (0.033 mL, 0.29 mmol) and the solution was heated at 100° C. under stirring for 16 hours. The solvent was then removed under reduced pressure and the crude purified by chromatography on a silica gel column (eluant dichloromethane/acetone) giving 31 mg of [8-(cyclohexylamino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazolin-3-yl](phenyl)methanone and 15 mg of [8-(cyclohexylamino)-1-methyl-1H-pyrazolo[4,3-h]quinazolin-3-yl](phenyl)methanone (70% yield overall).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe crude purified by chromatography on a silica gel column (eluant dichloromethane/acetone)

Sources & evidence

ORD record
ord-54ebdd2ab0684172b552d43eefd923c3
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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