Ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate → (3-(4-(Azetidin-1-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone

HRID 1035207Notes

Reaction equation

HRID 1035207 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:16]=[CH:15][C:9]([CH2:10][N:11]3[CH2:14][CH2:13][CH2:12]3)=[CH:8][CH:7]=2)[CH2:2]1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:29][C:28]([C:30](OCC)=[O:31])=[N:27][N:26]=2)=[CH:21][CH:20]=1>>[N:11]1([CH2:10][C:9]2[CH:15]=[CH:16][C:6]([O:5][CH:3]3[CH2:2][N:1]([C:30]([C:28]4[O:29][C:25]([C:22]5[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=5)=[N:26][N:27]=4)=[O:31])[CH2:4]3)=[CH:7][CH:8]=2)[CH2:12][CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 13407471Ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylateHCID 666534951-(4-(Azetidin-3-yloxy)benzyl)azetidine

Product 1

HCID 56598264(3-(4-(Azetidin-1-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanoneYield 68%

Procedure

Using a similar protocol as described in Example 36 employing 41A (0.10 g, 0.46 mmol) and ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate (0.13 g, 0.52 mmol) as starting materials afforded 130 mg (68%) of 41 as a solid. 1H NMR (500 MHz, CDCl3): δ 2.08 (m, 2H), 3.19 (t, 4H), 3.51 (s, 2H), 3.89 (s, 3H), 4.32 (d, 1H), 4.64 (dd, 1H), 4.74 (d, 1H), 5.06 (m, 1H), 5.11 (m, 1H), 6.72 (d, 2H), 7.02 (d, 2H), 7.21 (d, 2H), 8.10 (d, 2H), MS (APCI+) m/z 421 [M+H]+, LC purity: 95%.

Sources & evidence

ORD record
ord-17cfd2f691af4f06b27356a645f476f9
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

Loading…