1,3-Benzodioxol-4-amine → 4-(2,3-methylenedioxyanilino)-7-methoxy-5-(N-methylpiperidin-4-yloxy)quinazoline dihydrochloride

HRID 641723Notes

Reaction equation

HRID 641723 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.[CH2:22]1[O:31][C:30]2[C:24](=[C:25]([CH:27]=[CH:28][CH:29]=2)[NH2:26])[O:23]1>>[ClH:1].[ClH:1].[CH2:22]1[O:31][C:30]2[C:24](=[C:25]([CH:27]=[CH:28][CH:29]=2)[NH:26][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:20][CH3:21])=[CH:9][C:10]=3[O:12][CH:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)[N:5]=[CH:4][N:3]=2)[O:23]1

Participants

3

Reactant 2

HCID 103131651,3-Benzodioxol-4-amineHCID 113812714-Chloro-7-methoxy-5-[(1-methylpiperidin-4-yl)oxy]quinazoline

Product 1

HCID 119740184-(2,3-methylenedioxyanilino)-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 2,3-methylenedioxyaniline (J. Med. Chem., 1979, 2, 1354) 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) 2.0-2.1 (m, 2H), 2.15-2.3 (m, 4H), 2.31 (s, 3H), 2.85 (m, 2H), 3.91 (s, 3H), 6.01 (s, 2H), 6.5 (d, 1H), 6.68 (d, 1H), 6.82 (d, 1H), 6.91 (m, 1-1), 8.0 (d, 1H), 8.6 (s, 1H), 9.72 (s, 1H); Mass Spectrum: M+H+ 409.

Sources & evidence

ORD record
ord-8caf723549ce4e68bd951d8fd7df114a
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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