4-Chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline → 6-Methoxy-7-(3-pyrrolidin-1-ylpropoxy)4-(2-trifluoromethylindol-5-yloxy)quinazoline

HRID 1791585Notes

Reaction equation

HRID 1791585 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:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]([C:33]([F:36])([F:35])[F:34])=[CH:27]2>>[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:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]([C:33]([F:36])([F:34])[F:35])=[CH:27]2

Participants

3

Reactant 2

HCID 111417924-Chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazolineHCID 220307102-(Trifluoromethyl)-1h-indol-5-ol

Product 1

HCID 220305726-Methoxy-7-(3-pyrrolidin-1-ylpropoxy)4-(2-trifluoromethylindol-5-yloxy)quinazolineYield 71.9%

Procedure

Using an analogous procedure to that described in Example 44, 4-chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline (100 mg, 0.3 mmol), (prepared as described for the starting material in Example 9), was reacted with 5-hydroxy-2-trifluoromethylindole (75 mg, 0.37 mmol), (prepared as described for the starting material in Example 44), to give 6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)4-(2-trifluoromethylindol-5-yloxy)quinazoline (105 mg, 70%).

Workup

  1. custom(prepared
  2. custom(prepared

Sources & evidence

ORD record
ord-a3c232ef77384535b4420dbb140115b3
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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