3-methylazetidin-3-ol Hydrochloride → (3-(2-Chloro-4-((3-hydroxy-3-methylazetidin-1-yl)methyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

HRID 1035249Notes

Reaction equation

HRID 1035249 reaction equation
[Cl: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.Cl.[CH3:29][C:30]1([OH:34])[CH2:33][NH:32][CH2:31]1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][N:32]2[CH2:33][C:30]([OH:34])([CH3:29])[CH2:31]2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]1[CH2:12][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])[CH2:14]1

Participants

3

Reactant 2

HCID 115427813-methylazetidin-3-ol HydrochlorideHCID 580431283-Chloro-4-(1-(5-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde

Product 1

HCID 56598927(3-(2-Chloro-4-((3-hydroxy-3-methylazetidin-1-yl)methyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanoneYield 56%

Procedure

Using a similar protocol as described in Example 70 employing 78A and 3-methylazetidin-3-ol hydrochloride as starting materials afforded 34 mg (56%) of 78 as a solid. 1H NMR (500 MHz, CDCl3): δ 1.50 (s, 3H), 3.07 (d, 2H), 3.30 (d, 2H), 3.57 (s, 2H), 4.39 (m, 1H), 4.65 (m, 1H), 4.81 (m, 1H), 5.13 (m, 2H), 5.29 (s, 1H), 6.59 (m, 2H), 7.13 (d, 1H), 7.35 (s, 1H), 7.53 (t, 2H), 7.59 (t, 1H), 8.16 (d, 2H), MS (APCI+) m/z 455 [M+H]+, LC purity: 93%.

Sources & evidence

ORD record
ord-dcdfc95feb324ad4805b79a146fa17a9
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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