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

HRID 454100Notes

Reaction equation

HRID 454100 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-7f406c115e174636ac7345834832b7be
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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