4-Chloro-7-methoxy-6-(3-(4-morpholinyl)propoxy)quinazoline → HCID 86698283, compound

HRID 2408965Notes

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

Participants

Reactant 3

HCID 226492214-Chloro-7-methoxy-6-(3-(4-morpholinyl)propoxy)quinazoline

HCID 86698281DMF NaOH

HCID 866982845-(Tert-butyl)-2-nitroselenophene-3-ylamine

Product 1

HCID 86698283HCID 86698283, compound

Procedure

The reaction of 4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline with 5-(tert-butyl)-2-nitroselenophene-3-ylamine in the presence of DMF/NaOH as described in Example 1 gave title compound as a yellow color solid, mp 172-174° C. IR (KBr) vmax 3431, 2942, 2860, 1616, 1436, 1309, 1281, 1197, 1121, 1025, 863 cm−1; 1H NMR (400 MHz, CDCl3): δ 11.67 (1H, s, exchangeable with D2O), 8.90 (1H, s), 8.83 (1H, s), 7.30 (1H, s), 7.25 (1H, s), 4.30 (2H, t, J=6.2 Hz), 4.03 (3H, s), 3.73 (4H, t, J=4.4 Hz), 2.61 (2H, t, J=7.2 Hz), 2.51 (4H, br s), 2.14 (2H, pentet, J=6.6 Hz), 1.47 (9H, s); 13C NMR (100 MHz, CDCl3): δ 176.6, 156.0, 153.4, 152.8, 150.3, 148.4, 144.9, 130.1, 120.1, 109.9, 107.8, 99.8, 67.5, 67.0, 56.3, 55.4, 53.8, 37.9, 32.0, 26.1; LC-MS (positive ion mode): m/z 548, 550 (M+H)+.

Sources & evidence

ORD record: ord-033a59a2c84d4902990f8d7131cae73a
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815879B2

Reaction notes

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