Pyridine → 1-methyl-8-[(phenylacetyl)amino]-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide
Reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]3[C:12]([C:16]([NH2:18])=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1.N1C=CC=CC=1.[C:25]1([CH2:31][C:32](Cl)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[CH3:15][N:14]1[C:5]2[C:4]3[N:3]=[C:2]([NH:1][C:32](=[O:33])[CH2:31][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:6]=2[C:12]([C:16]([NH2:18])=[O:17])=[N:13]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
0.40 g (1.47 mmol) of 8-amino-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide were suspended in 20 mL of tetrahydrofuran and 5 mL of pyridine and 0.42 mL (3.22 mmol) of phenylacetylchloride were added. The reaction mixture was stirred at room temperature for 16 hours. The solvent was evaporated, the residue redissolved with dichloromethane, washed with aqueous NaHCO3 and then with water, After drying over anhydrous Na2SO4 the solvent was removed under reduced pressure and the crude purified by chromatography on a silica gel column (eluant cyclohexane/acetone) giving 0.35 mg of the title compound (60% yield).
Workup
- customThe solvent was evaporated
- dissolutionthe residue redissolved with dichloromethane
- washwashed with aqueous NaHCO3
- dry with materialwith water, After drying over anhydrous Na2SO4 the solvent
- customwas removed under reduced pressure
- customthe crude purified by chromatography on a silica gel column (eluant cyclohexane/acetone)
Sources & evidence
- ORD record
- ord-7b619c4dd58e4ca292f8d0fcdbf27617
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08981089B2
Reaction notes
Loading…