Trimethylamine → HCID 44201200, compound

HRID 1928674Notes

Reaction equation

HRID 1928674 reaction equation
[CH3:1][C:2]1[O:8][CH:7]=[C:6]([OH:9])[C:4](=[O:5])[CH:3]=1.CN(C)C.[F:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1>C1COCC1>[F:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([O:9][C:6]2[C:4](=[O:5])[CH:3]=[C:2]([CH3:1])[O:8][CH:7]=2)=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 678794-Fluorobenzoyl chlorideHCID 695214H-Pyran-4-one, 5-hydroxy-2-methyl-

Product 1

HCID 44201200HCID 44201200, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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 (840 μl) was added drop-wise and the contents stirred (˜5 min). 4-Fluorobenzoyl chloride (600 μl) 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 1.04 g crystalline product (4.19 mmol; 88% yield). This compound was found to have an EC50 of >1 mM. 1H NMR (DMSO-d6) δ 8.59 (s, 1H; 2-H); 8.18-8.13 (dd, 2H); 7.47-7.41 (t, 2H); 6.44 (s, 1H; 5-H); 2.34 (s, −3H; 6-CH3).

Workup

  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

Sources & evidence

ORD record
ord-623db59f0d884b569821e82987776c99
Source dataset
uspto-grants-2012_05
Patent number
US08183398B2

Reaction notes

Loading…