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

HRID 469519Notes

Reaction equation

HRID 469519 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:15].N1C=CC=CC=1.[C:22]12([CH2:32][C:33](Cl)=[O:34])[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2>C(Cl)Cl.CCOC(C)=O>[C:22]12([CH2:32][C:33]([NH:1][N:2]3[N:11]=[C:10]([CH:12]([CH3:13])[CH3:14])[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:3]3=[O:15])=[O:34])[CH2:29][CH:28]3[CH2:27][CH:26]([CH2:25][CH:24]([CH2:30]3)[CH2:23]1)[CH2:31]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 27718821-Adamantaneacetyl chlorideHCID 671616462-amino-4-isopropylphthalazin-1(2H)-one

Product 1

HCID 532368452-(1-adamantyl)-N-(4-isopropyl-1-oxophthalazin-2(1H)-yl)acetamideYield 87.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product of Example 1B (45.4 mg, 0.223 mmol), pyridine (0.023 mL, 0.28 mmol), and (adamantan-1-yl)acetyl chloride (0.052 g, 0.24 mmol) in CH2Cl2 (0.8 mL) was stirred for 2 hours, diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (eluted with 8% EtOAc/CH2Cl2) to give the title compound (0.0743 g, 0.196 mmol) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 11.09 (s, 1H), 8.35 (dd, 1H), 8.10 (d, 1H), 7.98 (td, 1H), 7.89 (ddd, 1H), 3.62 (quin, 1H), 2.03 (s, 2H), 1.95 (s, 3H), 1.76-1.52 (m, 12H), 1.26 (d, 6H); MS (ESI−) M/Z 378.1 (M−H)−.

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe residue was chromatographed on SiO2 (eluted with 8% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-437bde40e83145c0997c25a38b7336f0
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

Loading…