4-Chlorobenzylamine → HCID 67282408, compound

HRID 1616129Notes

Reaction equation

HRID 1616129 reaction equation
Cl[C:2]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:10](=[O:19])[C:9]2[C:4](=[CH:5][C:6]([C:20]([O:22][CH3:23])=[O:21])=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1>C(O)(C)C>[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH:39][C:2]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:10](=[O:19])[C:9]3[C:4](=[CH:5][C:6]([C:20]([O:22][CH3:23])=[O:21])=[CH:7][CH:8]=3)[N:3]=2)=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 660364-ChlorobenzylamineHCID 81531DiisopropylethylamineHCID 67283727HCID 67283727, compound

Product 1

HCID 67282408HCID 67282408, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of methyl 2-chloro-3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate (0.10 g, 0.23 mmol) in isopropyl alcohol (2.5 mL) was added N,N-diisopropylethylamine (84 μL, 0.48 mmol) and p-chlorobenzylamine (70 μL, 0.57 mmol). The reaction mixture was heated to 100° C. and stirred for 1 h. The mixture was then cooled to rt and concentrated. The residue was purified by flash silica gel chromatography (0% to 50% EtOAc/hexanes) to afford methyl 2-[(4-chlorobenzyl)amino]-3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate (46 mg, 44%). LC-MS: (FA) ES+ 456.

Workup

  1. temperatureThe mixture was then cooled to rt
  2. concentrationconcentrated
  3. customThe residue was purified by flash silica gel chromatography (0% to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-50019cc1c7df466bae85c6aa600b8058
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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