Sodium hydride → HCID 9825551, compound

HRID 855679Notes

Reaction equation

HRID 855679 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:24]1([C:30]2[CH2:34][C:33](=[O:35])[NH:32][N:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[H-].[Na+]>CN(C=O)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[N:5]=[CH:4][N:3]=[C:2]2[O:35][C:33]1[CH:34]=[C:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:31][N:32]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 785775-Phenyl-4H-pyrazol-3-olHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline

Product 1

HCID 9825551HCID 9825551, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using an analogous procedure to that described for Example 2, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (169 mg, 0.5 mmol), (prepared as described for the starting material in Example 2), was reacted with 3-phenyl-4,5-dihydro-1H-pyrazol-5-one (200 mg, 1.25 mmol), (J. Org. Chem., 1967, 32, 3321-3324), in the presence of sodium hydride (50 mg, 1.25 mmol, prewashed with pentane) in DMF (3 ml) to give 6-methoxy-7-(3-morpholinopropoxy)-4-(5-phenylpyrazol-3-yloxy)quinazoline as the free base. The free base was dissolved in a mixture of methylene chloride/methanol (1/1) and 3M hydrochloric acid in methanol was added. The volatiles were removed by evaporation to give 6-methoxy-7-(3-morpholinopropoxy)-4-(5-phenylpyrazol-3-yloxy)quinazoline hydrochloride (115 mg, 43%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-56e14469993944528029416adba02b26
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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