HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate | HCID 651752 | — |
| Reactant | 1-(4-(Azetidin-3-yloxy)phenyl)-N,N-dimethylmethanamine | HCID 66653120 | — |
| Product | (3-(4-((Dimethylamino)methyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone | HCID 56598126 | 38% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08546375B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-549298f641eb4277acf043f944c78e6b |
| Source note | uspto-grants-2013_10 |