4-Hydroxy-2-methylbenzaldehyde → 4-(1-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)-2-methylbenzaldehyde

HRID 1035244Notes

Reaction equation

HRID 1035244 reaction equation
CS([O:5][CH:6]1[CH2:9][N:8]([C:10]([C:12]2[O:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[N:15][N:16]=2)=[O:11])[CH2:7]1)(=O)=O.O[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[C:28]([CH3:34])[CH:27]=1>>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:14]2[O:13][C:12]([C:10]([N:8]3[CH2:9][CH:6]([O:5][C:26]4[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[C:28]([CH3:34])[CH:27]=4)[CH2:7]3)=[O:11])=[N:16][N:15]=2)=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 4581854-Hydroxy-2-methylbenzaldehydeHCID 580431311-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

Product 1

HCID 580431564-(1-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)-2-methylbenzaldehydeYield 67%

Procedure

Using a similar protocol as described in Example 71A employing 73B and 4-hydroxy-2-methylbenzaldehyde as starting materials afforded 9.4 g (67%) of 73C as a solid. 1H NMR (500 MHz, CDCl3): δ 2.67 (s, 3H), 3.89 (s, 3H), 4.37 (m, 1H), 4.70 (m, 1H), 4.78 (m, 1H), 5.15 (m, 2H), 6.65 (s, 1H), 6.74 (d, 1H), 7.02 (d, 2H), 7.78 (d, 1H), 8.11 (d, 2H), 10.2 (s, 1H).

Sources & evidence

ORD record
ord-ac9959718e744e7f826dac07957b91ab
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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