4-Chloro-6,7-bis(2-methoxyethoxy)quinazoline → 3-(6,7-Bis(2-methoxyethoxy)quinazolin-4-ylamino)-5-tert-butylselenophene-2-carboxamide
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[C:9]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:27]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[Se:25][C:24]=1[C:32]([NH2:34])=[O:33].CN(C=O)C.[OH-].[Na+]>>[CH3:16][O:15][CH2:14][CH2:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:17][CH2:18][CH2:19][O:20][CH3:21])[N:5]=[CH:4][N:3]=[C:2]2[NH:22][C:23]1[CH:27]=[C:26]([C:28]([CH3:31])([CH3:29])[CH3:30])[Se:25][C:24]=1[C:32]([NH2:34])=[O:33]Participants
Procedure
The reaction of 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline with 3-amino-5-tert-butylselenophene-2-carboxamide in the presence of DMF/NaOH as described in Example 1 gave title compound as a pale yellow color solid, mp 198-204° C. IR (KBr) vmax 3430, 3162, 2961, 1627, 1576, 1474, 1463, 1386, 1321, 1242, 1131, 1092, 937, 859 cm−1; 1H NMR (400 MHz, CDCl3): δ 12.63 (1H, s, exchangeable with D2O), 8.67 (1H, s), 8.64 (1H, s), 7.66 (2H, br s, exchangeable with D2O), 7.40 (1H, s), 7.28 (1H, s), 4.25-4.33 (4H, m), 3.75-3.80 (4H, m), 3.37 (3H, s), 3.36 (3H, s), 1.41 (9H, s); 13C NMR (100 MHz, CDCl3): δ 168.2, 167.4, 153.9, 153.8, 153.0, 148.6, 147.0, 146.0, 120.8, 112.1, 108.7, 108.6, 101.5, 70.0 (2C), 68.2, 68.0, 58.4, 58.3, 36.5, 32.2; LC-MS (positive ion mode): m/z 521, 523 (M+H)+.
Sources & evidence
- ORD record
- ord-eeb33659de6a4775bdd533e0e877fd47
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815879B2
Reaction notes
Loading…