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

Participants

Role	Name	HCID	Charge
Reactant	Ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate	HCID 13407471	—
Reactant	1-(4-(Azetidin-3-yloxy)-2-chlorophenyl)-N,N-dimethylmethanamine	HCID 66653489	—
Product	(3-(3-Chloro-4-((dimethylamino)methyl)phenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone	HCID 56598400	82%

Reaction Steps

Using a similar protocol as described in Example 16 employing 47A (70 mg, 0.29 mmol) and ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate (75 mg, 0.30 mmol) as starting materials afforded 105 mg (82%) of 47 as a solid. 1H NMR (500 MHz, CDCl3): δ 2.20 (s, 6H), 3.48 (s, 2H), 3.90 (s, 3H), 4.32 (dd, 1H), 4.65 (dd, 1H), 4.74 (dd, 1H), 5.06 (m, 1H), 5.13 (dd, 1H), 6.68 (dd, 1H), 6.80 (d, 1H), 7.02 (d, 2H), 7.35 (d, 1H), 8.10 (d, 2H), MS (APCI+) m/z 443 [M+H]+, LC purity: 91%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546375B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-4d036d7f5b4141089160f8778d77ec30
Source note	uspto-grants-2013_10