3-Methyl-4-(1-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde → (3-(4-((3-Ethyl-3-hydroxyazetidin-1-yl)methyl)-2-methylphenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

HRID 1035247Notes

Reaction equation

HRID 1035247 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:11]1[CH2:14][N:13]([C:15]([C:17]2[O:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:20][N:21]=2)=[O:16])[CH2:12]1)[CH:5]=O.FC(F)(F)C(O)=O.[CH2:35]([C:37]1([OH:41])[CH2:40][NH:39][CH2:38]1)[CH3:36]>>[CH2:35]([C:37]1([OH:41])[CH2:40][N:39]([CH2:5][C:4]2[CH:7]=[CH:8][C:9]([O:10][CH:11]3[CH2:14][N:13]([C:15]([C:17]4[O:18][C:19]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)=[N:20][N:21]=4)=[O:16])[CH2:12]3)=[C:2]([CH3:1])[CH:3]=2)[CH2:38]1)[CH3:36]

Participants

3

Reactant 2

HCID 580430913-Methyl-4-(1-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehydeHCID 666534471354792-80-5

Product 1

HCID 56598800(3-(4-((3-Ethyl-3-hydroxyazetidin-1-yl)methyl)-2-methylphenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanoneYield 11%

Procedure

Using a similar protocol as described in Example 70 employing 74A and 70A as starting materials afforded 35 mg (11%) of 74 as a solid. 1H NMR (500 MHz, CDCl3): δ 0.95 (t, 3H), 1.78 (q, 2H), 2.24 (s, 3H), 3.01 (d, 2H), 3.31 (d, 2H), 3.57 (s, 2H), 4.35 (m, 1H), 4.68 (m, 1H), 4.75 (m, 1H), 5.07 (m, 1H), 5.12 (m, 1H), 6.45 (d, 1H), 7.06 (d, 1H), 7.11 (s, 1H), 7.52 (t, 2H), 7.60 (t, 1H), 8.16 (d, 1H), MS (APCI+) m/z 449 [M+H]+, LC purity: 97%.

Sources & evidence

ORD record
ord-a8344d2c5cb54696b5e8f3fee7c4b2a0
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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