4-Chloro-7-methoxy-6-(3-(4-morpholinyl)propoxy)quinazoline → 3-(6-(3-Morpholinopropoxy)-7-methoxyquinazolin-4-ylamino)-5-tert-butylselenophene-2-carboxamide
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:22][CH3:23])=[C:9]([O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:24][C:25]1[CH:29]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[Se:27][C:26]=1[C:34]([NH2:36])=[O:35].CN(C=O)C.[OH-].[Na+]>>[O:19]1[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][CH2:13][O:12][C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][C:8]=2[O:22][CH3:23])[N:5]=[CH:4][N:3]=[C:2]3[NH:24][C:25]2[CH:29]=[C:28]([C:30]([CH3:33])([CH3:31])[CH3:32])[Se:27][C:26]=2[C:34]([NH2:36])=[O:35])[CH2:17][CH2:18]1Participants
Procedure
The reaction of 4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline with 3-amino-5-tert-butylselenophene-2-carboxamide in the presence of DMF/NaOH as described in Example 1 gave title compound a pale yellow color solid, mp 208-212° C. IR (KBr) vmax 3438, 3158, 2949, 1618, 1570, 1385, 1228, 1127, 1027, 859 cm−1; 1H NMR (400 MHz, CDCl3): δ 12.01 (1H, s, exchangeable with D2O), 8.86 (1H, s), 8.72 (1H, s), 7.38 (1H, s), 7.23 (1H, s), 5.37 (2H, br s), 4.32 (2H, t, J=6.4 Hz), 4.01 (3H, s), 3.73 (4H, t, J=4.6 Hz), 2.65 (2H, t, J=7.2 Hz), 2.51-2.52 (4H, m), 2.14 (2H, pentet, J=7.0 Hz), 1.47 (9H, s); 13C NMR (100 MHz, CDCl3): δ 168.9, 168.7, 155.2, 154.5, 153.4, 149.3, 148.2, 147.6, 121.8, 109.8, 109.2, 107.7, 101.4, 67.5, 67.0, 56.2, 55.5, 53.7, 37.2, 32.6, 26.2; LC-MS (negative ion mode): m/z 544, 546 (M−H)−.
Sources & evidence
- ORD record
- ord-b45bb204b8af48faa4f7d9c86217efed
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815879B2
Reaction notes
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