Reaktion #1122403

ord-79a32ed1ac814a6582118a53dcc77ae9

Reaktionsgleichung

CS(=O)(=O)OC1CN(C(=O)c2nnc(-c3ccccc3)o2)C1
53B
CS(=O)(=O)OC1CN(C(=O)c2nnc(-c3ccccc3)o2)C1
1-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate
Cc1cc(OC2CN(C(=O)c3nnc(-c4ccccc4)o3)C2)ccc1C=O
53C
Cc1cc(OC2CN(C(=O)c3nnc(-c4ccccc4)o3)C2)ccc1C=O
2-Methyl-4-(1-(5-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde
CCOC(=O)c1nnc(-c2ccc(OC)cc2)o1
ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate
COc1ccc(-c2nnc(C(=O)N3CC(Oc4ccc(C=O)cc4C)C3)o2)cc1
54A
Ausbeute 38.0%
COc1ccc(-c2nnc(C(=O)N3CC(Oc4ccc(C=O)cc4C)C3)o2)cc1
4-(1-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)-3-methylbenzaldehyde
Ausbeute 38.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Using similar protocols as described in Example 53A, 53B and 53C employing ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate as starting material afforded 0.37 g (38%) of 54A as a solid. 1H NMR (500 MHz, CDCl3): δ 2.32 (s, 3H), 3.89 (s, 3H), 4.36 (d, 1H), 4.72 (dd, 1H), 4.80 (d, 1H), 5.17 (m, 2H), 6.62 (d, 1H), 7.02 (d, 2H), 7.71 (d, 1H), 7.74 (s, 1H), 8.10 (d, 2H), 9.89 (s, 1H), MS (APCI+) m/z 394 [M+H]+.

Quelle

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