5-(4-Methoxyphenyl)-2,4-dihydro-3H-pyrazol-3-one → 4-(5-(4-Methoxyphenyl)pyrazol-3-yloxy)-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline

HRID 855735Notes

Reaction equation

HRID 855735 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH2:34][C:33](=[O:35])[NH:32][N:31]=2)=[CH:26][CH:25]=1>>[CH3:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[NH:31][N:32]=[C:33]([O:35][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)[CH:34]=2)=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 6053665-(4-Methoxyphenyl)-2,4-dihydro-3H-pyrazol-3-oneHCID 218748234-Chloro-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline

Product 1

HCID 179427534-(5-(4-Methoxyphenyl)pyrazol-3-yloxy)-6-methoxy-7-(3-methylsulphonylpropoxy)quinazolineYield 91%

Procedure

Using a procedure analogous to that described in Example 34, 4-chloro-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline (150 mg, 0.45 mol) was reacted with 3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-5-one (105 mg, 0.54 mol), (prepared as described for the starting material in Example 10), to give 4-(5-(4-methoxyphenyl)pyrazol-3-yloxy)-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline (220 mg, 91%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-1026d0db501a4c5b91c8434fb57d292b
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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