5-(4-Methoxyphenyl)-2,4-dihydro-3H-pyrazol-3-one → 4-(5-(4-Methoxyphenyl)pyrazol-3-yloxy)-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline

HRID 855731Notes

Reaction equation

HRID 855731 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][N:21]([CH3:24])[CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH2:37][C:36](=[O:38])[NH:35][N:34]=2)=[CH:29][CH:28]=1>>[CH3:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]2[NH:34][N:35]=[C:36]([O:38][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][N:21]([CH3:24])[CH2:20][CH2:19]5)=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)[CH:37]=2)=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 6053665-(4-Methoxyphenyl)-2,4-dihydro-3H-pyrazol-3-oneHCID 112450614-Chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline

Product 1

HCID 98061424-(5-(4-Methoxyphenyl)pyrazol-3-yloxy)-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazolineYield 43%

Procedure

Using a procedure analogous to that described in Example 14, 4-chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline (350 mg, 1 mol), (prepared as described for the starting material in Example 14), was reacted with 3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-5-one (380 mg, 2 mol), (prepared as described for the starting material in Example 10), to give 4-(5-(4-methoxyphenyl)pyrazol-3-yloxy)-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline (215 mg, 43%).

Workup

  1. custom(prepared
  2. custom(prepared

Sources & evidence

ORD record
ord-0eb8e976024a4b12ad0708c041e08a11
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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