Dimethylformamide → methyl N-[(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)acetyl]-N-methylglycinate

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Glycine, N-methyl-, methyl ester, hydrochloride (1:1)	HCID 83544	—
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 66678441	HCID 66678441	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	methyl N-[(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)acetyl]-N-methylglycinate	HCID 66678412	—

Reaction Steps

To a solution (3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)acetic acid (preparation described in Example 24 Step 1, 209 mg, 0.48 mmol) in DMF (2 mL) at 0° C. was added DIEA (252 μL, 1.5 mmol) and HATU (183 mg, 0.48 mmol). After 10 min, a solution of sarcosine methyl ester hydrochloride (74 mg, 0.53 mmol) in DMF (1 mL) was added and the reaction mixture stirred at RT overnight. EtOAc was added and the mixture was washed with water. The organic phase was then dried over MgSO4, filtered and concentrated in vacuo affording the title compound. LC/MS (Method B): 500.2 (M+H)+. HPLC (Method A) Rt 5.73 min (Purity: 98.9%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08815919B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-0651ec2d62214cbea4fdc8425a2ae5bc
Source note	uspto-grants-2014_08