Triethylamine → 2-(1-Adamantyloxycarbonyl)-4-(4-fluorophenyl)-5-[4-(Methylsulfonyl)phenyl]-3(2H)-pyridazinone

A solution of 4-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone, prepared according to the procedure of Example 11 (200 mg, 0.58 mmol) in CH2Cl2 (8 ml) was prepared and stirred. 1-Adamantylfluoroformate (172 mg, 0.87 mmol), dimethylaminopyridine (14 mg, 0.011 mmol) and triethylamine (0.12 ml, 0.87 mmol) were added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (50 ml) and washed with 10% citric acid (50 ml), brine (50 ml) and dried over MgSO4, and concentrated in vacuo. The resulting crude residue was purified using flash chromatography (SiO2, eluting with 15:1 CH2Cl2:diethyl ether) to provide the desired product (yield: 55 mg, 18%). 1H NMR (300 MHz, DMSO-d4) δ 1.66 (bs, 6H), 2.25 (bd, 10H), 3.21 (s, 3H), 7.15 (t, 2H), 7.24 (m, 2H), 7.6 (dd, 2H), 7.88 (d, J=9 Hz, 2H), 8.15 (s, 1H). MS (ESI) m/z 521 (M−H)+. Anal. calc. for C21H15F N2O3S2: C 64.35; H, 5.20; N, 5.36.

1. customwas prepared
2. stirringThe reaction mixture was stirred at room temperature overnight
3. washwashed with 10% citric acid (50 ml), brine (50 ml)
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vacuo
6. customThe resulting crude residue was purified
7. washflash chromatography (SiO2, eluting with 15:1 CH2Cl2:diethyl ether)

ORD record

ord-45eb83dcf6304d51b2d095b773308363

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07115591B2