Sodium hydride → HCID 9957456, compound

HRID 855706Notes

Reaction equation

HRID 855706 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.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH2:35][C:34](=[O:36])[NH:33][N:32]=2)=[CH:27][CH:26]=1.[H-].[Na+]>CN(C=O)C>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[NH:32][N:33]=[C:34]([O:36][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]5[CH2:23][CH2:22][O:21][CH2:20][CH2:19]5)=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)[CH:35]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 47787935-(4-Chloro-phenyl)-2,4-dihydro-pyrazol-3-oneHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline

Product 1

HCID 9957456HCID 9957456, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using an analogous procedure to that described for Example 9, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (140 mg, 0.415 mmol), (prepared as described for the starting material in Example 2), was reacted with 3-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-5-one (202 mg, 1.04 mmol) in the presence of sodium hydride (41.5 mg, 1.04 mmol, prewashed with THF) in DMF (2.5 ml) to give 4-(5-(4-chlorophenyl)pyrazol-3-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazoline (150 mg, 73%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-8e0072a9367c41b3a26b2728a3094443
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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