Pyridine → 2-(1-adamantyl)-N-(2-isopropyl-4-oxoquinazolin-3(4H)-yl)acetamide

HRID 1853397Notes

Reaction equation

HRID 1853397 reaction equation
[NH2:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]1[CH:13]([CH3:15])[CH3:14].[C:16]12([CH2:26][C:27](Cl)=[O:28])[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2.N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:16]12([CH2:26][C:27]([NH:1][N:2]3[C:11](=[O:12])[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[N:4]=[C:3]3[CH:13]([CH3:15])[CH3:14])=[O:28])[CH2:23][CH:22]3[CH2:21][CH:20]([CH2:19][CH:18]([CH2:24]3)[CH2:17]1)[CH2:25]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 27718821-Adamantaneacetyl chlorideHCID 51882113-Amino-2-isopropyl-4(3H)-quinazolinone

Product 1

HCID 498723352-(1-adamantyl)-N-(2-isopropyl-4-oxoquinazolin-3(4H)-yl)acetamideYield 41.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Amino-2-isopropyl-4(3H)-quinazolinone (Aldrich, 97.5 mg, 0.48 mmol) was dissolved in chloroform (5 mL). 1-Adamantaneacetyl chloride (107.0 mg, 0.50 mmol) and pyridine (100 μL, 1.24 mmol) were added, and the reaction was allowed to stir at ambient temperature for 22 hours. The reaction mixture was concentrated and the residue was purified by preparative HPLC on a Waters Nova-Pak® HR C18 6 μm 60 {acute over (Å)} Prep-Pak® cartridge column (40 mm×100 mm) using a gradient of 10% to 100% acetonitrile in 10 mM aqueous ammonium acetate over 12 minutes at a flow rate of 70 mL/min to provide the title compound as a white solid (76.4 mg, 22%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.21-1.26 (m, 6H), 1.60-1.75 (m, 12H), 1.94-1.99 (m, 3H), 2.09-2.20 (m, 2H), 3.09-3.18 (m, 1H), 7.50-7.55 (m, 1H), 7.67 (d, J=7.5 Hz, 1H), 7.82-7.88 (m, 1H), 8.12 (dd, J=7.9, 1.2 Hz, 1H), 10.80 (s, 1H) ppm; MS (DCI/NH3) m/z 380 (M+H)+; Elemental Analysis: Calculated for C23H29N3O2: C, 72.79; H, 7.70; N, 11.07. Found: C, 72.79; H, 7.81; N, 11.07.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by preparative HPLC on a Waters Nova-Pak® HR
  3. customover 12 minutes

Sources & evidence

ORD record
ord-1fff1034c6da4f2fb1382de326937ecd
Source dataset
uspto-grants-2015_02
Patent number
US08962639B2

Reaction notes

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