Ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate → (3-(3-Chloro-4-((dimethylamino)methyl)phenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone

HRID 1035211Notes

Reaction equation

HRID 1035211 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][N:13]([CH3:15])[CH3:14])=[C:8]([Cl:16])[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>>[Cl:16][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[CH2:12][N:13]([CH3:14])[CH3:15])[O:5][CH:3]1[CH2:4][N:1]([C:30]([C:28]2[O:29][C:25]([C:22]3[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=3)=[N:26][N:27]=2)=[O:31])[CH2:2]1

Participants

3

Reactant 2

HCID 13407471Ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylateHCID 666534891-(4-(Azetidin-3-yloxy)-2-chlorophenyl)-N,N-dimethylmethanamine

Product 1

HCID 56598400(3-(3-Chloro-4-((dimethylamino)methyl)phenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanoneYield 82%

Procedure

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%.

Sources & evidence

ORD record
ord-4d036d7f5b4141089160f8778d77ec30
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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