Reaktion #1122398

ord-8b329c9d0e394d0388eb9e8130f3b43d

Reaktionsgleichung

COc1c(CN2CCCC2)ccc(OC2CNC2)c1C
52B
COc1c(CN2CCCC2)ccc(OC2CNC2)c1C
1-(4-(Azetidin-3-yloxy)-2-methoxy-3-methylbenzyl)pyrrolidine
CCOC(=O)c1nnc(-c2ccc(OC)cc2)o1
ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate
COc1ccc(-c2nnc(C(=O)N3CC(Oc4ccc(CN5CCCC5)c(OC)c4C)C3)o2)cc1
52
Ausbeute 37.2%
COc1ccc(-c2nnc(C(=O)N3CC(Oc4ccc(CN5CCCC5)c(OC)c4C)C3)o2)cc1
(3-(3-M ethoxy-2-methyl-4-(pyrrolidin-1-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone
Ausbeute 37.2%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Using a similar protocol as described in Example 16 employing 52B (0.25 g, 0.90 mmol) and ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate (0.34 g, 1.36 mmol) as starting materials afforded 160 mg (37%) of 52 as a solid. 1H NMR (500 MHz, CDCl3): δ 1.77 (s, 4H), 2.19 (s, 3H), 2.52 (s, 4H), 3.60 (s, 2H), 3.76 (s, 3H), 3.89 (s, 3H), 4.35 (dd, 1H), 4.66 (dd, 1H), 4.75 (dd, 1H), 5.07 (m, 1H), 5.13 (dd, 1H), 6.29 (d, 1H), 7.02 (d, 2H), 7.17 (d, 1H), 8.10 (d, 2H), MS (APCI+) m/z 479 [M+H]+, LC purity: 95%.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08546375B2uspto-grants-2013_10