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

HRID 1035246Notes

Reaction equation

HRID 1035246 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][CH:20]=[CH:19][CH:18]=3)=[N:15][N:16]=2)=[O:11])[CH2:7]1)(=O)=O.O[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][C:25]=1[CH3:32]>>[CH3:32][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:24]=1[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][CH:20]=[CH:19][CH:18]=3)=[N:15][N:16]=2)=[O:11])[CH2:7]1)[CH:28]=[O:29]

Participants

3

Reactant 2

HCID 1399014-Hydroxy-3-methylbenzaldehydeHCID 580430991-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

Product 1

HCID 580430913-Methyl-4-(1-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehydeYield 28%

Procedure

Using a similar protocol as described in Example 71A employing 53B and 4-hydroxy-3-methylbenzaldehyde as starting materials afforded 0.8 g (28%) of 74A as a solid. 1H NMR (500 MHz, CDCl3): δ 2.33 (s, 3H), 4.40 (m, 1H), 4.71 (m, 1H), 4.82 (m, 1H), 5.19 (m, 2H), 6.61 (s, 1H), 7.54 (t, 2H), 7.60 (t, 1H), 7.73 (d, 1H), 7.75 (s, 1H), 8.18 (d, 2H), 9.89 (s, 1H).

Sources & evidence

ORD record
ord-3207763b1e824c939bfb8374862e598f
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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