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

HRID 875108
Notes
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Reaction equation

HRID 875108 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 materialwith water, After 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-7b619c4dd58e4ca292f8d0fcdbf27617
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08981089B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes