4-Chloro-7-methoxy-6-(3-(4-morpholinyl)propoxy)quinazoline → 3-(6-(3-Morpholinopropoxy)-7-methoxyquinazolin-4-ylamino)-5-phenyl-selenophene-2-carboxamide

HRID 2408968Notes

Reaction equation

HRID 2408968 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]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[Se:27][C:26]=1[C:36]([NH2:38])=[O:37].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]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[Se:27][C:26]=2[C:36]([NH2:38])=[O:37])[CH2:17][CH2:18]1

Participants

4

Reactant 3

HCID 226492214-Chloro-7-methoxy-6-(3-(4-morpholinyl)propoxy)quinazolineHCID 866468873-Amino-5-phenylselenophene-2-carboxamideHCID 86698281DMF NaOH

Product 1

HCID 866982873-(6-(3-Morpholinopropoxy)-7-methoxyquinazolin-4-ylamino)-5-phenyl-selenophene-2-carboxamide

Procedure

The reaction of 4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline with 3-amino-5-phenylselenophene-2-carboxamide in the presence of DMF/NaOH as described in Example 1 gave title compound as a yellow color solid, mp 236-240° C. IR (KBr) vmax 34369, 3158, 2935, 1635, 1579, 1387, 1321, 1238, 1216, 1145, 1113, 902, 846 cm−1; 1H NMR (400 MHz, DMSO-d6): δ 12.50 (1H, s), 9.16 (1H, s), 8.65 (1H, s), 7.77 (2H, br s), 7.68-7.70 (2H, m), 7.44-7.52 (3H, m), 7.39 (1H, s), 7.26 (1H, s), 4.20 (2H, br s), 3.96 (3H, s), 3.58 (4H, br s), 2.50 (2H, br s), 2.40 (4H, br s), 2.00 (2H, pentet, J=6.5 Hz); LC-MS (positive ion mode): m/z 566, 568 (M+H)+.

Sources & evidence

ORD record
ord-f8d49fb5cb6f4518bd1e454b97383ab8
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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