Diisopropylethylamine → 4-(4-Fluorobenzyloxy)-1-(2-(4-ethyloxazol-5-yl)-1-methyl-1h-benzo[d]imidazol-6-yl)pyridin-2(1h)-one

https://huagongshe.com/reaction/2203028

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	4-Ethyl-1,3-oxazole-5-carboxylic acid	HCID 53434643	—
Reactant	1-(4-Amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one	HCID 89690279	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-(4-Fluorobenzyloxy)-1-(2-(4-ethyloxazol-5-yl)-1-methyl-1h-benzo[d]imidazol-6-yl)pyridin-2(1h)-one	HCID 89702579	17.7%

Reaction Steps

A mixture of 1-(4-amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (67.9 mg), 4-ethyl-1,3-oxazole-5-carboxylic acid (28.2 mg), HATU (80.0 mg), N,N-diisopropylethylamine (0.105 ml) and DMF (2.0 ml) was stirred at room temperature for 2 h. The mixture was poured into saturated NaHCO3 solution and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated in vacuo. The residue was dissolved in AcOH (1.5 ml), and the mixture was stirred at 80° C. for 1 h. The mixture was concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH). The resulting solid was recrystallized from EtOAc-hexane to give the title compound (15.7 mg) as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09365540B2
Source dataset	uspto-grants-2016_06
ORD ID	ord-27518b4adc924c468e89ccb7913ade3f
Source note	uspto-grants-2016_06