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

HRID 1853399Notes

Reaction equation

HRID 1853399 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]=[CH:3]1.[C:13]12([CH2:23][C:24](Cl)=[O:25])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2.N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:13]12([CH2:23][C:24]([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]=[CH:3]3)=[O:25])[CH2:20][CH:19]3[CH2:18][CH:17]([CH2:16][CH:15]([CH2:21]3)[CH2:14]1)[CH2:22]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 631253-Amino-4(3H)-quinazolinoneHCID 27718821-Adamantaneacetyl chloride

Product 1

HCID 498724332-(1-adamantyl)-N-(4-oxoquinazolin-3(4H)-yl)acetamideYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Amino-4(3H)-quinazolinone (158.7 mg, 0.99 mmol) was dissolved in chloroform (5 mL). 1-Adamantaneacetyl chloride (204.1 mg, 0.96 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® 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 (264.9 mg, 82%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.60-1.69 (m, 12H), 1.96 (br s, 3H), 7.58-7.63 (m, 1H), 7.74 (d, J=8.3 Hz, 1H), 7.87-7.93 (m, 1H), 8.18-8.20 (m, 2H), 11.12 (s, 1H) ppm; MS (DCI/NH3) m/z 338 (M+H)+; Elemental Analysis: Calculated for C20H23N3O2: C, 71.19; H, 6.87; N, 12.45. Found: C, 71.11; H, 6.85; N, 12.43.

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-a04d62fa05704d18a79f168119dd0c77
Source dataset
uspto-grants-2015_02
Patent number
US08962639B2

Reaction notes

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