Diisopropylethylamine → N-(5-bromo-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide

HRID 406841Notes

Reaction equation

HRID 406841 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]([NH:17][C:18]3[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[Br:36][C:37]1[CH:38]=[CH:39][C:40]([CH3:44])=[C:41]([CH:43]=1)[NH2:42]>O1CCCC1>[Br:36][C:37]1[CH:38]=[CH:39][C:40]([CH3:44])=[C:41]([NH:42][C:22](=[O:23])[C:21]2[CH:20]=[CH:19][C:18]([NH:17][C:9]3[N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]=3)=[CH:26][CH:25]=2)[CH:43]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27348055-Bromo-o-toluidineHCID 576629364-(4-Phenylquinazolin-2-ylamino)benzoyl chloride

Product 1

HCID 57662893N-(5-bromo-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamideYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-phenylquinazolin-2-ylamino)benzoyl chloride (1.0 g, 2.8 mmol) and Hunig's base (600 μL, 3.4 mmol) in tetrahydrofuran (25 mL) was added 5-bromo-2-methylaniline (600 mg, 3.2 mmol), and the reaction was allowed to stir at rt overnight. The mixture was concentrated on a rotary evaporator and purified by flash column chromatography to give N-(5-bromo-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide (1.0 g, 70%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.34 (s, 1H), 9.77 (s, 1H), 8.18 (d, 2), 7.98 (d, 2H), 7.82 (m, 6H), 7.65 (m, 4H), 7.41 (dt, 1H), 7.35 (dd, 1H), 7.25 (d, 1H), 2.24 (s, 3H). MS (EI) for C28H21BrN4O: 511.2 (MH+).

Workup

  1. concentrationThe mixture was concentrated on a rotary evaporator
  2. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-8aef7f11cd35488fa147f009705c3b56
Source dataset
uspto-grants-2014_06
Patent number
US08754092B2

Reaction notes

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