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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1035203Generated: October 31, 2026

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

https://huagongshe.com/reaction/1035203

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl 5-phenyl-1,3,4-oxadiazole-2-carboxylateHCID 651752—
Reactant1-(4-(Azetidin-3-yloxy)phenyl)-N,N-dimethylmethanamineHCID 66653120—
Product(3-(4-((Dimethylamino)methyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanoneHCID 5659812638%

Reaction Steps

Using a similar protocol as described in Example 16 employing 33B (0.10 g, 0.48 mmol) and ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.12 g, 0.53 mmol) as starting materials afforded 69 mg (38%) of 33 as a solid. 1H NMR (500 MHz, CDCl3): δ 2.24 (s, 6H), 3.37 (s, 2H), 4.34 (dd, 1H), 4.65 (dd, 1H), 4.77 (dd, 1H), 5.10 (m, 2H), 6.74 (d, 2H), 7.24 (m, 2H), 7.55 (m, 3H), 8.15 (d, 2H), MS (APCI+) m/z 379 [M+H]+, LC purity: 95%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08546375B2
Source datasetuspto-grants-2013_10
ORD IDord-549298f641eb4277acf043f944c78e6b
Source noteuspto-grants-2013_10