4-Chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline → 6-Methoxy-4-(2-methylindol-6yloxy)-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline

HRID 454119Notes

Reaction equation

HRID 454119 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[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:23][C:24]1[CH:32]=[C:31]2[C:27]([CH:28]=[C:29]([CH3:33])[NH:30]2)=[CH:26][CH:25]=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[CH2:22][CH2:21][CH2:20][CH2:19]1)[N:5]=[CH:4][N:3]=[C:2]2[O:23][C:24]1[CH:32]=[C:31]2[C:27]([CH:28]=[C:29]([CH3:33])[NH:30]2)=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 111417924-Chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazolineHCID 148785962-Methyl-1H-indol-6-ol

Product 1

HCID 220308626-Methoxy-4-(2-methylindol-6yloxy)-7-(3-(pyrrolidin-1-yl)propoxy)quinazolineYield 85%

Procedure

Using an analogous procedure to that described for Example 121, 4-chloro-6-methoxy-7-(3-pyrrolidinopropoxy)quinazoline (150 mg, 0.47 mmol), (prepared as described for the starting material in Example 9), was reacted with 6-hydroxy-2-methylindole (83 mg, 0.56 mol), (Eur. J. Med. Chem. 1975, 10, 187), to give 6-methoxy-4-(2-methylindol-6-yloxy)-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (170 mg, 85%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-cf116bc390bf4eba8eb2ef733a27e069
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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