4-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline → 4-(3-Bromo-6-chlorobenzofuran-7-ylamino)-6-methoxy-7-(3-morpholinopropoxy)quinazoline

HRID 22784Notes

Reaction equation

HRID 22784 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[C:33]2[O:32][CH:31]=[C:30]([Br:34])[C:29]=2[CH:28]=[CH:27][C:26]=1[Cl:35]>>[Br:34][C:30]1[C:29]2[CH:28]=[CH:27][C:26]([Cl:35])=[C:25]([NH:24][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]5[CH2:23][CH2:22][O:21][CH2:20][CH2:19]5)=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)[C:33]=2[O:32][CH:31]=1

Participants

3

Reactant 2

HCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolineHCID 225914827-Amino-3-bromo-6-chlorobenzofuran

Product 1

HCID 102308824-(3-Bromo-6-chlorobenzofuran-7-ylamino)-6-methoxy-7-(3-morpholinopropoxy)quinazolineYield 66.4%

Procedure

Using an analogous procedure to that described in Example 3, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (0.13 g) was reacted with 7-amino-3-bromo-6-chlorobenzofuran (0.186 g) to give the title compound (0.14 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 2.3 (m, 2H), 3.15 (m, 2H), 3.35 (t, 2H), 3.55 (m, 2H), 3.7 (t, 2H), 4.0 (s, 3H), 4.05 (m, 2H), 4.35 (t, 2H), 7.4 (s, 1H), 7.7 (d, 2H), 8.2 (s, 1H), 8.4 (s, 1H), 8.85 (s, 1H); Mass Spectrum: M+H+ 549.

Sources & evidence

ORD record
ord-fbfe61929760480f9609444663a8a6d7
Source dataset
uspto-grants-2005_02
Patent number
US06849625B2

Reaction notes

Loading…