2-Amino-4,5-dimethoxybenzamide → 2-(4-(Bis(2-hydroxyethyl)amino)phenyl)-6,7-dimethoxyquinazolin-4(3H)-one

HRID 336696Notes

Reaction equation

HRID 336696 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[OH:15][CH2:16][CH2:17][N:18]([C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1)[CH2:19][CH2:20][OH:21].COC1C=C(OC)C=C2C=1C(=O)NC(C1C=CC=CN=1)=N2>>[OH:15][CH2:16][CH2:17][N:18]([CH2:19][CH2:20][OH:21])[C:22]1[CH:29]=[CH:28][C:25]([C:26]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][C:9]([O:11][CH3:12])=[C:8]([O:13][CH3:14])[CH:7]=3)[N:1]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 108672362-Amino-4,5-dimethoxybenzamideHCID 128249654-(N,N-Bis(2-hydroxyethyl)amino)benzaldehydeHCID 1360379985,7-dimethoxy-2-(pyridin-2-yl)quinazolin-4(3H)-one

Product 1

HCID 1360379642-(4-(Bis(2-hydroxyethyl)amino)phenyl)-6,7-dimethoxyquinazolin-4(3H)-oneYield 24%

Procedure

2-(4-(Bis(2-hydroxyethyl)amino)phenyl)-6,7-dimethoxyquinazolin-4(3H)-one was synthesized from 2-amino-4,5-dimethoxy-benzamide and 4-(N,N-bis(2-hydroxyethyl)amino)benzaldehyde, using the method described for 5,7-dimethoxy-2-(pyridin-2-yl)quinazolin-4(3H)-one. 2-(4-(Bis(2-hydroxyethyl)amino)phenyl)-6,7-dimethoxyquinazolin-4(3H)-one (72 mg, 24%) was isolated as a yellow solid. Selected data: MS (m/z): 386.15; MP 268-270° C.

Sources & evidence

ORD record
ord-24d64564efa7409698ec027ee972a298
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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