4-Chloro-2-(4-chlorophenyl)-6,7-dimethoxyquinazoline → 3-(2-(4-Chlorophenyl)-6,7-dimethoxyquinazolin-4-ylamino)-5-tert-butylselenophene-2-carboxamide

HRID 2408998Notes

Reaction equation

HRID 2408998 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[N:3]=1.[NH2:23][C:24]1[CH:28]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[Se:26][C:25]=1[C:33]([NH2:35])=[O:34].CN(C=O)C.[OH-].[Na+]>>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:4]2[N:3]=[C:2]([NH:23][C:24]3[CH:28]=[C:27]([C:29]([CH3:32])([CH3:30])[CH3:31])[Se:26][C:25]=3[C:33]([NH2:35])=[O:34])[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 229973614-Chloro-2-(4-chlorophenyl)-6,7-dimethoxyquinazolineHCID 866468893-Amino-5-tert-butylselenophene-2-carboxamideHCID 86698281DMF NaOH

Product 1

HCID 866983103-(2-(4-Chlorophenyl)-6,7-dimethoxyquinazolin-4-ylamino)-5-tert-butylselenophene-2-carboxamide

Procedure

The reaction of 4-chloro-2-(4-chlorophenyl)-6,7-dimethoxyquinazoline with 3-amino-5-tert-butylselenophene-2-carboxamide in the presence of DMF/NaOH as described in Example 1 gave title compound as a white color solid, mp 268-270° C. 1H NMR (400 MHz, CDCl3): δ 12.03 (1H, s, exchangeable with D2O), 9.05 (1H, s), 8.49 (2H, d, J=8.4 Hz), 7.45 (2H, d, J=8.4 Hz), 7.37 (1H, s), 7.32 (1H, s), 5.37 (2H, s, exchangeable with D2O), 4.11 (3H, s), 4.06 (3H, s), 1.52 (9H, s); 13C NMR (100 MHz, CDCl3): δ 168.6, 168.5, 158.1, 155.0, 154.8, 149.9, 148.5, 148.1, 137.7, 136.0, 129.4, 128.5, 122.0, 109.3, 108.4, 108.0, 100.3, 56.3, 56.2, 37.3, 32.7; LC-MS (negative ion mode): m/z 541, 543, 545 (M−H)−.

Sources & evidence

ORD record
ord-b4b71e8b3d7244a893726e1aa6b927f1
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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