N,N-Dimethylglycine → methyl-6-(4-(3-(methylamino)propoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	N,N-Dimethylglycine	HCID 673	—
Reactant	Diisopropylethylamine	HCID 81531	—
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	HCID 49862146	HCID 49862146	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	methyl-6-(4-(3-(methylamino)propoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile	HCID 59410673	—

Reaction Steps

1-Methyl-6-(4-(2-(piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (0.188 g), 2-(dimethylamino)acetic acid (0.090 g) and DIPEA (0.362 ml) were dissolved in NMP (2.5 ml) and HATU (0.250 g) was then added. The reaction was stirred at room temperature for 16 hours. The reaction mixture was diluted with EtOAc (30 mL) and washed with saturated sodium bicarbonate solution. Organics were dried over sodium sulphate to yield crude. Purification by flash chromatography (10 g SiO2 column, DCM to 5% MeOH in DCM gradient) afforded methyl-6-(4-(3-(methylamino)propoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile. (59 mg)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08026236B2
Source dataset	uspto-grants-2011_09
ORD ID	ord-38d61f1b99f749d5854c005a1a3ab341
Source note	uspto-grants-2011_09