3-amino-N,N-dimethylbenzylamine → N-(3-dimethylaminomethylphenyl)-2-[4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]acetamide

HRID 1690479Notes

Reaction equation

HRID 1690479 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](O)=[O:24])=[CH:18][CH:17]=1.[CH3:26][N:27]([CH2:29][C:30]1[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=1)[NH2:33])[CH3:28]>>[CH3:28][N:27]([CH2:29][C:30]1[CH:31]=[C:32]([NH:33][C:23](=[O:24])[CH2:22][C:19]2[CH:18]=[CH:17][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][N:7]=3)=[CH:21][CH:20]=2)[CH:34]=[CH:35][CH:36]=1)[CH3:26]

Participants

3

Reactant 2

HCID 992943-amino-N,N-dimethylbenzylamineHCID 669066322-[4-(6,7-Dimethoxyquinazolin-4-yloxy)phenyl]acetic acid

Product 1

HCID 66906690N-(3-dimethylaminomethylphenyl)-2-[4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]acetamideYield 86%

Procedure

Using an analogous procedure to that described in Example 1, 2-[4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]acetic acid was reacted with 3-dimethylaminomethylaniline to give the title compound in 86% yield; 1H NMR: (DMSOd6) 2.14 (s, 3H), 3.35 (s, 2H), 3.68 (s, 2H), 3.97 (s, 3H), 3.99 (s, 3H), 6.96 (d, 1H), 7.24 (m, 1H), 7.26 (d, 2H), 7.39 (s, 1H), 7.44 (d, 2H), 7.53 (d, 1H), 7.55 (d, 1H), 7.58 (s, 1H), 8.53 (s, 1H), 10.19 (s, 1H); Mass Spectrum: M+H+ 473.

Sources & evidence

ORD record
ord-00db25b057db4a5cae4238eb690dbfed
Source dataset
uspto-grants-2012_04
Patent number
US08153643B2

Reaction notes

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