4-Chlorobenzylamine → HCID 67282467, compound

HRID 1616132Notes

Reaction equation

HRID 1616132 reaction equation
Cl[C:2]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10](=[O:18])[C:9]2[C:4](=[CH:5][C:6]([C:19]([O:21][CH3:22])=[O:20])=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[Cl:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH2:38])=[CH:35][CH:34]=1>C(O)(C)C>[Cl:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH:38][C:2]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10](=[O:18])[C:9]3[C:4](=[CH:5][C:6]([C:19]([O:21][CH3:22])=[O:20])=[CH:7][CH:8]=3)[N:3]=2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 660364-ChlorobenzylamineHCID 81531DiisopropylethylamineHCID 67283428HCID 67283428, compound

Product 1

HCID 67282467HCID 67282467, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of methyl 2-chloro-4-oxo-3-phenyl-3,4-dihydroquinazoline-7-carboxylate (0.10 g, 0.25 mmol) in isopropyl alcohol (2.8 mL) was added N,N-diisopropylethylamine (93 μL, 0.53 mmol) and p-chlorobenzylamine (77.3 μL, 0.64 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 30% EtOAc/hexanes) to afford methyl 2-[(4-chlorobenzyl)amino]-4-oxo-3-phenyl-3,4-dihydroquinazoline-7-carboxylate (30 mg, 30%). LC-MS: (FA) ES+ 420.

Workup

  1. temperatureThe mixture was then cooled to rt
  2. concentrationconcentrated
  3. customThe residue was purified by flash silica gel chromatography (0% to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7e425ed527b04f44946cdb24633a3ef8
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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