Reaktion #1122393

ord-4d036d7f5b4141089160f8778d77ec30

Reaktionsgleichung

CN(C)Cc1ccc(OC2CNC2)cc1Cl
47A
CN(C)Cc1ccc(OC2CNC2)cc1Cl
1-(4-(Azetidin-3-yloxy)-2-chlorophenyl)-N,N-dimethylmethanamine
CCOC(=O)c1nnc(-c2ccc(OC)cc2)o1
ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate
COc1ccc(-c2nnc(C(=O)N3CC(Oc4ccc(CN(C)C)c(Cl)c4)C3)o2)cc1
47
Ausbeute 82.0%
COc1ccc(-c2nnc(C(=O)N3CC(Oc4ccc(CN(C)C)c(Cl)c4)C3)o2)cc1
(3-(3-Chloro-4-((dimethylamino)methyl)phenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone
Ausbeute 82.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

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%.

Quelle

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