4-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline → HCID 66906826, compound

HRID 1690498Notes

Reaction equation

HRID 1690498 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=2[O:19][CH3:20])=[N:7][CH:8]=1.Cl[C:24]1[C:33]2[C:28](=[CH:29][C:30]([O:36][CH2:37][CH2:38][O:39][CH3:40])=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][N:25]=1>>[CH3:22][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:24]3[C:33]4[C:28](=[CH:29][C:30]([O:36][CH2:37][CH2:38][O:39][CH3:40])=[C:31]([O:34][CH3:35])[CH:32]=4)[N:27]=[CH:26][N:25]=3)=[CH:14][C:13]=2[O:19][CH3:20])=[N:7][CH:8]=1

Participants

3

Reactant 2

HCID 107306534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazolineHCID 66906648HCID 66906648, compound

Product 1

HCID 66906826HCID 66906826, compoundYield 74%

Procedure

Using an analogous procedure to that described in Example 15, N-(5-dimethylaminopyridin-2-yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide was reacted with 4-chloro-7-(2-methoxyethoxy)-6-methoxyquinazoline. There was thus obtained the title compound in 74% yield; 1H NMR: (CDCl3) 2.93 (s, 6H), 3.5 (s, 3H), 3.75 (s, 2H), 3.88-3.93 (m, 2H), 3.91 (s, 3H), 4.05 (s, 3H), 4.32-4.38 (m, 2H), 6.86 (s, 1H), 6.87 (m, 1H), 7.10 (m, 1H), 7.33 (s, 1H), 7.4 (d, 1H), 7.53 (d, 1H), 7.73 (d, 1H), 8.09 (d, 1H), 8.18 (br s, 1H), 8.63 (s, 1H); Mass Spectrum: M+H+ 534.

Sources & evidence

ORD record
ord-73c621fb736546c89d29f4f8a9bc6354
Source dataset
uspto-grants-2012_04
Patent number
US08153643B2

Reaction notes

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