3-methylazetidin-3-ol Hydrochloride → (3-(2-Chloro-4-((3-hydroxy-3-methylazetidin-1-yl)methyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

Participants

Role	Name	HCID	Charge
Reactant	3-methylazetidin-3-ol Hydrochloride	HCID 11542781	—
Reactant	3-Chloro-4-(1-(5-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde	HCID 58043128	—
Product	(3-(2-Chloro-4-((3-hydroxy-3-methylazetidin-1-yl)methyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone	HCID 56598927	56%

Reaction Steps

Using a similar protocol as described in Example 70 employing 78A and 3-methylazetidin-3-ol hydrochloride as starting materials afforded 34 mg (56%) of 78 as a solid. 1H NMR (500 MHz, CDCl3): δ 1.50 (s, 3H), 3.07 (d, 2H), 3.30 (d, 2H), 3.57 (s, 2H), 4.39 (m, 1H), 4.65 (m, 1H), 4.81 (m, 1H), 5.13 (m, 2H), 5.29 (s, 1H), 6.59 (m, 2H), 7.13 (d, 1H), 7.35 (s, 1H), 7.53 (t, 2H), 7.59 (t, 1H), 8.16 (d, 2H), MS (APCI+) m/z 455 [M+H]+, LC purity: 93%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546375B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-dcdfc95feb324ad4805b79a146fa17a9
Source note	uspto-grants-2013_10