4-Chlorobenzylamine → HCID 67281627, compound

HRID 1616135Notes

Reaction equation

HRID 1616135 reaction equation
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=2)[N:10]=[C:9]1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH: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>[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=2)[N:10]=[C:9]1[NH:39][CH2:38][C:37]1[CH:40]=[CH:41][C:34]([Cl:33])=[CH:35][CH:36]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 660364-ChlorobenzylamineHCID 81531DiisopropylethylamineHCID 67282899HCID 67282899, compound

Product 1

HCID 67281627HCID 67281627, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of methyl 3-benzyl-2-chloro-4-oxo-3,4-dihydroquinazoline-7-carboxylate (0.20 g, 0.37 mmol) in isopropyl alcohol (4 mL) was added N,N-diisopropylethylamine (0.13 mL, 0.77 mmol) and p-chlorobenzylamine (0.11 mL, 0.91 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 80% EtOAc/hexanes) to afford methyl 3-benzyl-2-[(4-chlorobenzyl)amino]-4-oxo-3,4-dihydroquinazoline-7-carboxylate (0.12 g, 75%). LC-MS: (FA) ES+434.

Workup

  1. temperatureThe mixture was then cooled to rt
  2. concentrationconcentrated
  3. customThe residue was purified by flash silica gel chromatography (0% to 80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3ae136f6f55a433dbf844bc9cbc6f8bb
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

Loading…