Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate → (3-(4-((Dimethylamino)methyl)-2,3-difluorophenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

Participants

Role	Name	HCID	Charge
Reactant	Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate	HCID 651752	—
Reactant	1-(4-(azetidin-3-yloxy)-2,3-difluorophenyl)-N,N-dimethylmethanamine dihydrochloride	HCID 67016452	—
Product	(3-(4-((Dimethylamino)methyl)-2,3-difluorophenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone	HCID 56598262	15.7%

Reaction Steps

Using a similar protocol as described in Example 36 employing 39A (0.32 g, 1.00 mmol) and ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.24 g, 1.10 mmol) as starting materials afforded 65 mg (15%) of 39 as a solid. 1H NMR (500 MHz, CDCl3): δ 2.27 (s, 6H), 3.46 (s, 2H), 4.39 (dd, 1H), 4.65 (dd, 1H), 4.82 (m, 1H), 5.13 (m, 2H), 6.52 (t, 1H), 7.04 (t, 1H), 7.54 (t, 2H), 7.60 (t, 1H), 8.16 (d, 2H), MS (APCI+) m/z 415 [M+H]+, LC purity: 89%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546375B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-f5e600eda33b4a70a4394298643fcc74
Source note	uspto-grants-2013_10