Trimethylamine → HCID 44201202, compound

Allomaltol (600 mg; 4.76 mmol) was weighed out into a round bottom flask (100 ml) containing a stir-bar. The contents were diluted with anhydrous THF (˜20 ml) and stirred (˜5 min) to afford a solution. Next, trimethyl amine (833 μl; 6.33 mmol; 1.33 equiv.) was added drop-wise and the contents stirred (˜5 min). Octanoyl chloride (770 μl; 724 mg; 4.45 mmol) was then added drop-wise, capped and stirred at room temperature. The reaction was monitored via silica gel TLC. Once complete, the reaction mixture was concentrated under reduced pressure and the contents purified by silica gel chromatography to afford 1.01 g of light yellow crystalline product (4.00 mmol; 90% yield). This compound was found to have an EC50 of 532 μM. 1H NMR (DMSO-d6) δ 8.39 (s, 1H; 2-H); 6.35 (s, 1H; 5-H); 2.54-2.52 (t, 2H); 2.29 (s, 3H; 6-CH3); 1.60-1.58 (p, 2H); 1.34-1.31 (m, 2H), 1.31-1.24 (m, 6H); 0.87-0.85 (t, 3H; —CH3).

1. addition(100 ml) containing a stir-bar
2. customto afford a solution
3. stirringthe contents stirred (˜5 min)
4. customcapped
5. stirringstirred at room temperature
6. concentrationOnce complete, the reaction mixture was concentrated under reduced pressure
7. customthe contents purified by silica gel chromatography

ORD record

ord-eb96766cb6dd4f3ebb9c32a061da9a5c

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08183398B2