Methoxyacetaldehyde → 7-(1-(2-Methoxyethyl)piperidin-4-ylmethoxy)-4(2-methylindol-5-yloxy)quinazoline

HRID 1791633Notes

Reaction equation

HRID 1791633 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([O:11][C:12]1[C:21]3[C:16](=[CH:17][C:18]([O:22][CH2:23][CH:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)=[CH:19][CH:20]=3)[N:15]=[CH:14][N:13]=1)=[CH:6][CH:5]=2.[CH3:30][O:31][CH2:32][CH:33]=O>>[CH3:30][O:31][CH2:32][CH2:33][N:27]1[CH2:28][CH2:29][CH:24]([CH2:23][O:22][C:18]2[CH:17]=[C:16]3[C:21]([C:12]([O:11][C:7]4[CH:8]=[C:9]5[C:4](=[CH:5][CH:6]=4)[NH:3][C:2]([CH3:1])=[CH:10]5)=[N:13][CH:14]=[N:15]3)=[CH:20][CH:19]=2)[CH2:25][CH2:26]1

Participants

3

Reactant 2

HCID 91563MethoxyacetaldehydeHCID 220308754-(2-Methylindol-5-yloxy)-7-(piperidin-4-ylmethoxy)quinazoline

Product 1

HCID 220306247-(1-(2-Methoxyethyl)piperidin-4-ylmethoxy)-4(2-methylindol-5-yloxy)quinazolineYield 46.4%

Procedure

Using an analogous procedure to that described for Example 71, 4-(2-methylindol-5-yloxy)-7-(piperidin-4-ylmethoxy)quinazoline (150 mg, 0.386 mmol), (prepared as described in Example 122), was reacted with methoxyacetaldehyde (83 mg, 0.772 mmol), (prepared as described for the starting material in Example 71), to give 7-(1-(2-methoxyethyl)piperidin-4-ylmethoxy)-4(2-methylindol-5-yloxy)quinazoline (80 mg, 46%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-950ddb65fb7545d7ae9e374e2c9a5445
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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