4-Chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline → 4-(2,4-Dimethylquinolin-7-yloxy)-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline

HRID 454029Notes

Reaction equation

HRID 454029 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:23][C:24]1[CH:33]=[C:32]([CH3:34])[C:31]2[C:26](=[CH:27][C:28]([OH:35])=[CH:29][CH:30]=2)[N:25]=1>>[CH3:23][C:24]1[CH:33]=[C:32]([CH3:34])[C:31]2[C:26](=[CH:27][C:28]([O:35][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]5[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]5)=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)=[CH:29][CH:30]=2)[N:25]=1

Participants

3

Reactant 2

HCID 117822304-Chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolineHCID 1354887037-Hydroxy-2,4-dimethylquinoline

Product 1

HCID 220305424-(2,4-Dimethylquinolin-7-yloxy)-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolineYield 33%

Procedure

Using a procedure analogous to that described for Example 9, 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (0.13 g, 0.4 mol), (prepared as described for the starting material in Example 10), was reacted with 2,4-dimethyl-7-hydroxyquinoline (87 mg, 0.5 mmol), (Chem. Berichte, 1903, 36, 4016), to give 4-(2,4-dimethylquinolin-7-yloxy)-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (61 mg, 33%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-0b7e4a82c8e04544a4adfa11822bcc58
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

Loading…