5-[(DIMETHYLAMINO)METHYL]-2-FUROIC ACID synthesis

Yield:-

Reaction Conditions:

Stage #1:dimethyl amine with sodium hydride in N,N-dimethyl-formamide at 20; for 0.5 h;
Stage #2:5-Chloromethyl-furan-2-carboxylic acid ethyl ester in N,N-dimethyl-formamide for 48 h;
Stage #3: with sodium hydroxide;water in ethanol at 80; for 0.666667 h;

Steps:

0. 16ml of a 2 M solution of dimethylamine was added to a stirred suspension of 19.2 mg of sodium hydride in 2 mL of DMF under a nitrogen atmosphere at room temperature for 30 min. Then a solution of 5-chloromethyl-furan-2-carboxylic acid ethyl ester in 2 mL of DMF was added dropwise over a period of 30 min. The reaction was then allowed to stir for 2 days. The solvent was then removed in vacuo and 5 mL of EtOH and 0. 35ml of 2 M NaOH added and stirred at 80 °C for 40 min. Upon return the reaction was acidified below pH 5.0 and the solvent removed in vacuo to produce the title compound to be hydrolysed and then used crude in the next stage

References:

ARROW THERAPEUTICS LIMITED WO2005/89771, 2005, A1 Location in patent:Page/Page column 38