2-(4-Chlorophenyl)ethylamine → HCID 67283095, compound

HRID 1616118Notes

Reaction equation

HRID 1616118 reaction equation
Cl[C:2]1[N:11]([CH3:12])[C:10](=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]([O:16][CH3:17])=[O:15])[CH:8]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][NH2:36])=[CH:30][CH:29]=1>C(O)(C)C>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][NH:36][C:2]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:14]([O:16][CH3:17])=[O:15])[CH:8]=3)[N:3]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 674302-(4-Chlorophenyl)ethylamineHCID 81531DiisopropylethylamineHCID 67282040HCID 67282040, compound

Product 1

HCID 67283095HCID 67283095, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of methyl 2-chloro-3-methyl-4-oxo-3,4-dihydroquinazoline-6-carboxylate (77.0 mg, 0.30 mmol) in isopropyl alcohol (5 mL) was added N,N-diisopropylethylamine (0.11 mL, 0.64 mmol) and 2-(4-chlorophenyl)ethanamine (0.11 mL, 0.76 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 5% MeOH/DCM) to afford methyl 2-{[2-(4-chlorophenyl)ethyl]amino}-3-methyl-4-oxo-3,4-dihydroquinazoline-6-carboxylate (106 mg, 94%). LC-MS: (FA) ES+ 372.

Workup

  1. temperatureThe mixture was then cooled to rt
  2. concentrationconcentrated
  3. customThe residue was purified by flash silica gel chromatography (0% to 5% MeOH/DCM)

Sources & evidence

ORD record
ord-896bd2b3ce7445488231bf22f8956c9f
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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