1-(4-(3-Hydroxypropyl)piperazin-1-yl)ethan-1-one → 6-(3-(4-Acetylpiperazin-1-yl)propoxy)-4-(7-azaindol-5-yloxy)-7-methoxyquinazoline

HRID 916388Notes

Reaction equation

HRID 916388 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[C:20]4[C:15](=[CH:16][C:17]([O:22][CH3:23])=[C:18]([OH:21])[CH:19]=4)[N:14]=[CH:13][N:12]=3)=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[C:24]([N:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35]O)[CH2:29][CH2:28]1)(=[O:26])[CH3:25]>>[C:24]([N:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][O:21][C:18]2[CH:19]=[C:20]3[C:15](=[CH:16][C:17]=2[O:22][CH3:23])[N:14]=[CH:13][N:12]=[C:11]3[O:10][C:6]2[CH:5]=[C:4]3[C:9](=[N:8][CH:7]=2)[NH:1][CH:2]=[CH:3]3)[CH2:29][CH2:28]1)(=[O:26])[CH3:25]

Participants

3

Reactant 2

HCID 114467711-(4-(3-Hydroxypropyl)piperazin-1-yl)ethan-1-oneHCID 589602364-(7-Azaindol-5-yloxy)-6-hydroxy-7-methoxyquinazohne

Product 1

HCID 589602286-(3-(4-Acetylpiperazin-1-yl)propoxy)-4-(7-azaindol-5-yloxy)-7-methoxyquinazolineYield 53.4%

Procedure

Using an analogous procedure to that described for the preparation of Example 2, 4-(7-azaindol-5-yloxy)-6-hydroxy-7-methoxyquinazoline (0.133 g, 0.432 mmol), (prepared as described for the starting material in Example 2), was reacted with 3-(4-acetylpiperazin-1-yl)propan-1-ol (0.097, 0.51 mmol), (prepared as described for the starting material in Example 1 or Example 7), to give 6-(3-(4-acetylpiperazin-1-yl)propoxy)-4-(7-azaindol-5-yloxy)-7-methoxyquinazoline (0.11 g, 53%).

Workup

  1. custom(prepared
  2. custom(prepared

Sources & evidence

ORD record
ord-6fa47f6c6b264103a969da79ae8aecf8
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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