4-(Dimethylamino)benzoic acid → HCID 23144247, compound

Participants

Role	Name	HCID	Charge
Reactant	4-(Dimethylamino)benzoic acid	HCID 12092	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Reactant	2-Amino-4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazole	HCID 86612468	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 23144247	HCID 23144247	3%

Reaction Conditions

Temperature	80 °C

Reaction Steps

Compound 454 (125 mg, 0.450 mmol) was dissolved in DMF (2 mL), and 4-(dimethylamino)benzoic acid (296 mg, 1.80 mmol), EDC hydrochloride (344 mg, 1.80 mmol) and 1-hydroxybenzotriazole monohydrate (276 mg, 1.80 mmol) were added thereto, followed by stirring at 80° C. for 2 hours. Water (200 mL) was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was purified through silica gel column chromatography (chloroform:methanol=9:1), followed by reslurrying with ethanol to afford the entitled Compound 465 (5.30 mg, 3%) as a pale brown solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08889718B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-085f6fc3139b40f8a2820f687f555f21
Source note	uspto-grants-2014_11