4-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline → 6-Methoxy-4-(2-methylindol-6-yloxy)-7-(3-morpholinopropoxy)quinazoline

HRID 454104Notes

Reaction equation

HRID 454104 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.[OH:24][C:25]1[CH:33]=[C:32]2[C:28]([CH:29]=[C:30]([CH3:34])[NH:31]2)=[CH:27][CH:26]=1>>[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:24][C:25]1[CH:33]=[C:32]2[C:28]([CH:29]=[C:30]([CH3:34])[NH:31]2)=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolineHCID 148785962-Methyl-1H-indol-6-ol

Product 1

HCID 220308986-Methoxy-4-(2-methylindol-6-yloxy)-7-(3-morpholinopropoxy)quinazolineYield 73%

Procedure

Using an analogous procedure to that described for Example 121, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (160 mg, 0.47 mol), (prepared as described for the starting material in Example 1), was reacted with 6-hydroxy-2-methylindole (84 mg, 0.57 mol), (Eur. J. Med. Chem. 1975, 10, 187), to give 6-methoxy-4-(2-methylindol-6-yloxy)-7-(3-morpholinopropoxy)quinazoline (157 mg, 73%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-f56fd016c71b459d94803ccc2862dd02
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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