4-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline → HCID 86698285, compound

HRID 2408966Notes

Reaction equation

HRID 2408966 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[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:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH2:15][O:14][C:8]2[CH:7]=[C:6]3[C:11]([C:2]([NH:24][C:25]4[CH:29]=[C:28]([C:30]([CH3:33])([CH3:31])[CH3:32])[Se:27][C:26]=4[C:34]([NH2:36])=[O:35])=[N:3][CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])[CH2:19][CH2:20]1

Participants

4

Reactant 3

HCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolineHCID 866468893-Amino-5-tert-butylselenophene-2-carboxamideHCID 86698281DMF NaOH

Product 1

HCID 86698285HCID 86698285, compound

Procedure

The reaction of 4-chloro-7-(3-morpholinopropoxy)-6-methoxyquinazoline 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 216-220° C. IR (KBr) vmax 3342, 3120, 2957, 2853, 1633, 1572, 1497, 1457, 1393, 1315, 1234, 1141, 1113, 1021, 903, 854, 798 cm1; 1H NMR (400 MHz, CDCl3): δ 12.06 (1H, s, exchangeable with D2O), 8.86 (1H, s), 8.71 (1H, s), 7.34 (1H, s), 7.25 (1H, s), 5.57 (2H, s, exchangeable with D2O), 4.25 (2H, t, J=6.6 Hz), 4.06 (3H, s), 3.74 (4H, t, J=4.4 Hz), 2.59 (2H, t, J=7.2 Hz), 2.51 (4H, br s), 2.10-2.16 (2H, m), 1.46 (9H, s); 13C NMR (100 MHz, CDCl3): δ 168.9, 168.6, 154.4, 154.3, 153.3, 150.1, 148.1, 147.4, 121.7, 109.6, 109.2, 108.3, 100.3, 67.3, 66.8, 56.2, 55.3, 53.7, 37.2, 32.6, 25.9; LC-MS (positive ion mode): m/z 546, 548 (M+H)+.

Sources & evidence

ORD record
ord-93898568b5464646921a19b904dc7b75
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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