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

HRID 1035216Notes

Reaction equation

HRID 1035216 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:17]=[CH:16][C:9]([CH2:10][N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[C:8]([O:18][CH3:19])[C:7]=2[CH3:20])[CH2:2]1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[O:33][C:32]([C:34](OCC)=[O:35])=[N:31][N:30]=2)=[CH:25][CH:24]=1>>[CH3:19][O:18][C:8]1[C:7]([CH3:20])=[C:6]([CH:17]=[CH:16][C:9]=1[CH2:10][N:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)[O:5][CH:3]1[CH2:4][N:1]([C:34]([C:32]2[O:33][C:29]([C:26]3[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=3)=[N:30][N:31]=2)=[O:35])[CH2:2]1

Participants

3

Reactant 2

HCID 13407471Ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylateHCID 666559581-(4-(Azetidin-3-yloxy)-2-methoxy-3-methylbenzyl)pyrrolidine

Product 1

HCID 56598402(3-(3-M ethoxy-2-methyl-4-(pyrrolidin-1-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanoneYield 37.2%

Procedure

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%.

Sources & evidence

ORD record
ord-8b329c9d0e394d0388eb9e8130f3b43d
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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