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 1035251Notes

Reaction equation

HRID 1035251 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][C:25](OC)=[CH:24][CH:23]=3)=[N:20][N:21]=2)=[O:16])[CH2:12]1)[CH:5]=O.Cl.[CH3:31][C:32]1([OH:36])[CH2:35][NH:34][CH2:33]1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][N:34]2[CH2:35][C:32]([OH:36])([CH3:31])[CH2:33]2)[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:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:20][N:21]=2)=[O:16])[CH2:12]1

Participants

3

Reactant 2

HCID 115427813-methylazetidin-3-ol HydrochlorideHCID 580431413-Chloro-4-(1-(5-(4-methoxyphenyl)-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 31%

Procedure

Using a similar protocol as described in Example 70 employing 79A and 3-methylazetidin-3-ol hydrochloride as starting materials afforded 29 mg (31%) of 79 as a solid. 1H NMR (500 MHz, CDCl3): δ 1.51 (s, 3H), 3.04 (d, 2H), 3.28 (d, 2H), 3.57 (s, 2H), 3.89 (s, 3H), 4.41 (m, 1H), 4.65 (m, 1H), 4.80 (m, 1H), 5.10 (m, 2H), 5.30 (s, 1H), 7.01 (d, 2H), 7.13 (s, 1H), 7.36 (s, 1H), 8.09 (d, 2H), MS (APCI+) m/z 485 [M+H]+, LC purity: 88%.

Sources & evidence

ORD record
ord-c80d99d234e14bb093a180cec6881e00
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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