4-Chloro-7-methoxy-5-[(1-methylpiperidin-4-yl)oxy]quinazoline → 4-(3-chlorobenzofuran-7-ylamino)-7-methoxy-5-(N-methylpiperidin-4-yloxy)quinazoline dihydrochloride

HRID 641722Notes

Reaction equation

HRID 641722 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:20][CH3:21])=[CH:9][C:10]=2[O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[N:5]=[CH:4][N:3]=1.[NH2:22][C:23]1[C:31]2[O:30][CH:29]=[C:28]([Cl:32])[C:27]=2[CH:26]=[CH:25][CH:24]=1>>[ClH:1].[ClH:32].[Cl:32][C:28]1[C:27]2[CH:26]=[CH:25][CH:24]=[C:23]([NH:22][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:20][CH3:21])=[CH:9][C:10]=4[O:12][CH:13]4[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]4)[N:5]=[CH:4][N:3]=3)[C:31]=2[O:30][CH:29]=1

Participants

3

Reactant 2

HCID 113812714-Chloro-7-methoxy-5-[(1-methylpiperidin-4-yl)oxy]quinazolineHCID 221407493-Chloro-1-benzofuran-7-amine

Product 1

HCID 221408364-(3-chlorobenzofuran-7-ylamino)-7-methoxy-5-(N-methylpiperidin-4-yloxy)quinazoline dihydrochloride

Procedure

Using an analogous procedure to that described in Example 5, 4-chloro-7-methoxy-5-(N-methylpiperidin-4-yloxy)quinazoline was reacted with 7-amino-3-chlorobenzofuran to give the title compound, a portion of which was treated with a saturated methanolic ammonia solution. The mixture was filtered and the filtrate was evaporated to give the free base; NMR Spectrum: (CDCl3) 2.0-2.4 (m, 6H), 2.33 (s, 3H), 2.9 (m, 2H), 3.93 (s, 3H), 4.6 (m, 1H), 6.56 (s, 1H), 6.9 (s, 1H), 7.3-7.4 (m, 2H), 7.7 (br s, 1H), 8.64 (s, 1H), 8.7 (d, 1H), 10.3 (br s, 1H); Mass Spectrum: M+H+ 439 and 441.

Sources & evidence

ORD record
ord-31e8dfe3d7a94290a76029b107ba2db4
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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