Ethyl 5-(4-(difluoromethoxy)phenyl)-1,3,4-oxadiazole-2-carboxylate → (5-(4-(Difluoromethoxy)phenyl)-1,3,4-oxadiazol-2-yl)(3-(4-((dimethylamino)methyl)phenoxy)azetidin-1-yl)methanone

Participants

Role	Name	HCID	Charge
Reactant	Ethyl 5-(4-(difluoromethoxy)phenyl)-1,3,4-oxadiazole-2-carboxylate	HCID 58043152	—
Reactant	1-(4-(Azetidin-3-yloxy)phenyl)-N,N-dimethylmethanamine	HCID 66653120	—
Product	(5-(4-(Difluoromethoxy)phenyl)-1,3,4-oxadiazol-2-yl)(3-(4-((dimethylamino)methyl)phenoxy)azetidin-1-yl)methanone	HCID 56598129	15.2%

Reaction Steps

Using a similar protocol as described in Example 36 employing 33B (0.19 g, 0.92 mmol) and 37A (0.26 g, 0.92 mmol) as starting materials afforded 62 mg (15%) of 37 as a solid. 1H NMR (500 MHz, CDCl3): δ 2.27 (s, 6H), 3.44 (s, 2H), 4.35 (dd, 1H), 4.66 (dd, 1H), 4.77 (dd, 1H), 5.10 (m, 2H), 6.62 (t, 1H), 6.75 (d, 2H), 7.28 (m, 4H), 8.19 (d, 2H), MS (APCI+) m/z 445 [M+H]+, LC purity: 94%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546375B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-34319c8878214f28bbbeb1495f56b669
Source note	uspto-grants-2013_10