4-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline → HCID 22732313, compound

HRID 2084025Notes

Reaction equation

HRID 2084025 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:24][C:25]1[CH:26]=[C:27]([NH:32][C:33](=[O:42])[C:34]2[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=2)[CH:28]=[CH:29][C:30]=1[CH3:31]>>[C:40]([C:37]1[CH:36]=[CH:35][C:34]([C:33]([NH:32][C:27]2[CH:28]=[CH:29][C:30]([CH3:31])=[C:25]([CH:26]=2)[NH:24][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)=[O:42])=[CH:39][CH:38]=1)#[N:41]

Participants

3

Reactant 2

HCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolineHCID 22057994HCID 22057994, compound

Product 1

HCID 22732313HCID 22732313, compoundYield 52%

Procedure

Using an analogous procedure to that described in Example 26, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline was reacted with N-(3-amino-4-methylphenyl)-4-cyanobenzamide to give the title compound in 52% yield; NMR: 2.15 (s, 3H), 2.3 (m, 2H), 3.0-4.1 (broad m, 10H), 3.95 (s, 3H), 4.3 (m, 2H), 7.35 (m, 2H), 7.65 (m, 1H), 7.88 (m, 1H), 8.02 (m, 2H), 8.14 (m, 3H), 8.53 (s, 1H), 10.65 (s, 1H), 12.1 (s, 1H); m/s: M+H+ 553.

Sources & evidence

ORD record
ord-a8e6fafed1dc488684dbf1c452aac98b
Source dataset
uspto-grants-2004_04
Patent number
US06716847B2

Reaction notes

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