2'-Aminoacetophenone → 8-[(2-acetylphenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 1914739Notes

Reaction equation

HRID 1914739 reaction equation
[C:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])(=[O:3])[CH3:2].I[C:12]1[N:21]=[CH:20][C:19]2[CH2:18][CH2:17][C:16]3[C:22]([C:26]([NH2:28])=[O:27])=[N:23][N:24]([CH3:25])[C:15]=3[C:14]=2[N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][C:12]1[N:21]=[CH:20][C:19]2[CH2:18][CH2:17][C:16]3[C:22]([C:26]([NH2:28])=[O:27])=[N:23][N:24]([CH3:25])[C:15]=3[C:14]=2[N:13]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 110862'-AminoacetophenoneHCID 11430Potassium CarbonateHCID 442356528-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Product 1

HCID 468869578-[(2-acetylphenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamideYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Palladium acetate Pd(OAc)2 (20 mg, 0.09 mmol), (±)-BINAP (55 mg, 0.09 mmol) and dimethylformamide (5 mL) were charged in a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. The mixture was stirred under argon for 30 minutes and added to a mixture of 2-acetylaniline (0.162 ml, 1.35 mmol), 8-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (319 mg, 0.9 mmol), potassium carbonate (1.24 g, 9 mmol) in dimethylformamide (10 mL). The resulting mixture was stirred at 80° C. for 4 hours under argon. After cooling to room temperature, the reaction mixture was filtered on a pad of celite. The solvent was concentrated, the crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 90/10) to afford 153 mg (47% yield) of the title compound.

Workup

  1. customflushed with argon
  2. customThe flask was evacuated
  3. stirringThe resulting mixture was stirred at 80° C. for 4 hours under argon
  4. filtrationthe reaction mixture was filtered on a pad of celite
  5. concentrationThe solvent was concentrated
  6. customthe crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 90/10)

Sources & evidence

ORD record
ord-e8405148e21a41c39871e51a205faa3e
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

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