2-Fluoroethanol → N-(5-chloro-1,3-benzodioxol-4-yl)-7-(2-fluoroethoxy)-5-[(1-methylpiperidin-4-yl)oxy]quinazolin-4-amine

HRID 641780Notes

Reaction equation

HRID 641780 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:27])=[CH:16][C:17]=3[O:19][CH:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[N:12]=[CH:11][N:10]=2)=[C:6]2[O:28][CH2:29][O:30][C:5]2=[CH:4][CH:3]=1.[F:31][CH2:32][CH2:33]O>>[Cl:1][C:2]1[C:7]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:27][CH2:33][CH2:32][F:31])=[CH:16][C:17]=3[O:19][CH:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[N:12]=[CH:11][N:10]=2)=[C:6]2[O:28][CH2:29][O:30][C:5]2=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 97372-FluoroethanolHCID 1355107014-(6-chloro-2,3-methylenedioxyanilino)-7-hydroxy-5-(N-methylpiperidin-4-yloxy)quinazoline

Product 1

HCID 11974120N-(5-chloro-1,3-benzodioxol-4-yl)-7-(2-fluoroethoxy)-5-[(1-methylpiperidin-4-yl)oxy]quinazolin-4-amine

Procedure

Using an analogous procedure to that described in Example 51, 4-(6-chloro-2,3-methylenedioxyanilino)-7-hydroxy-5-(N-methylpiperidin-4-yloxy)quinazoline was reacted with 2-fluoroethanol to give the title compound; NMR Spectrum: (CDCl3) 2.0-2.1 (m, 2H), 2.15-2.3 (m, 2H), 2.35 (s, 3H), 2.3-2.4 (m, 2H), 2.8 (br s, 2H), 4.32 (m, 1H), 4.4 (m, 1H), 4.65 (m, 1H), 4.8 (m, 1H), 4.9 (m, 1H), 6.05 (s, 2H), 6.6 (s, 1H), 6.75 (d, 1H), 6.85 (s, 1H), 7.0 (d, 1H), 8.55 (s, 1H), 9.3 (s, 1H); Mass Spectrum: M+H+ 475 and 477.

Sources & evidence

ORD record
ord-ff70383ca1734e2d8def5dbcaa3b17fd
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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