Pyridine → 1-methyl-8-[(phenylacetyl)amino]-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 1455103Notes

Reaction equation

HRID 1455103 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]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 574441008-amino-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Product 1

HCID 689312841-methyl-8-[(phenylacetyl)amino]-1H-pyrazolo[4,3-h]quinazoline-3-carboxamideYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customThe solvent was evaporated
  2. dissolutionthe residue redissolved with dichloromethane
  3. washwashed with aqueous NaHCO3
  4. dry with materialAfter drying over anhydrous Na2SO4 the solvent
  5. customwas removed under reduced pressure
  6. customthe crude purified by chromatography on a silica gel column (eluant cyclohexane/acetone)

Sources & evidence

ORD record
ord-d5fb2c00119e4f22b70d3c2249a5cbc2
Source dataset
uspto-grants-2009_01
Patent number
US07482354B2

Reaction notes

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