Dimethylamine → 2-(2-chloro-4-{2-[(1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}phenyl)-N,N-dimethylacetamide

Participants

Role	Name	HCID	Charge
Reactant	Dimethylamine	HCID 674	—
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	(2-chloro-4-{2-[(1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}phenyl)acetic acid	HCID 89582113	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(2-chloro-4-{2-[(1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}phenyl)-N,N-dimethylacetamide	HCID 89583978	—

Reaction Steps

(2-chloro-4-{2-[(1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}phenyl)acetic acid (50 mg, 109 mmol) was dissolved in DMF (1 ml) and dimethylamine (0.163 g, 0.326 mmol), DIEA (0.057 ml, 0.326 mmol), and HATU (62 mg, 0.163 mmol) added. The mixture was stirred at RT overnight. The solution was loaded directly onto a Biotage RP C18 cartridge (30 g) and purified using a gradient eluant of 10-100% water:acetonitrile+0.05% formic acid. The volatiles were removed in vacuo to afford the title compound. LC/MS (m/z): 487 (M+H)+. GPR119 Human EC50: 2.3 nM.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09018224B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-1fb604cdc75a4365bee5b5301ef48629
Source note	uspto-grants-2015_04