Ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate → 1-{-4-[(1-{[5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]carbonyl}azetidin-3-yl)oxy]-2-methylphenyl}-N,N-dimethylmethanamine

HRID 1035187Notes

Reaction equation

HRID 1035187 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]([CH3:16])[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>>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[O:29][C:28]([C:30]([N:1]3[CH2:2][CH:3]([O:5][C:6]4[CH:11]=[CH:10][C:9]([CH2:12][N:13]([CH3:15])[CH3:14])=[C:8]([CH3:16])[CH:7]=4)[CH2:4]3)=[O:31])=[N:27][N:26]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 13407471Ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylateHCID 666563501-(4-(Azetidin-3-yloxy)-2-methylphenyl)-N,N-dimethylmethanamine

Product 1

HCID 565978511-{-4-[(1-{[5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]carbonyl}azetidin-3-yl)oxy]-2-methylphenyl}-N,N-dimethylmethanamineYield 74.6%

Procedure

Using a similar protocol as described in Example 16 employing 20C (0.16 g, 0.73 mmol) and ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate (0.20 g, 0.80 mmol) as starting materials afforded 0.23 g (74%) of 20 as a solid. 1H NMR (600 MHz, CDCl3): δ 2.21 (s, 6H), 2.33 (s, 3H), 3.30 (s, 2H), 3.87 (s, 3H), 4.27-4.35 (m, 1H), 4.58-4.66 (m, 1H), 4.69-4.76 (m, 1H), 5.00-5.15 (m, 2H), 6.53 (d, 1H), 6.58 (s, 1H), 7.00 (d, 2H), 7.14 (d, 1H), 8.08 (d, 2H), MS (APCI+) m/z 423 [M+H]+, LC purity: 98%.

Sources & evidence

ORD record
ord-b299493243444089881fa09046faba4f
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

Loading…