HCID 58043115, compound → (3-(4-((3-Ethyl-3-hydroxyazetidin-1-yl)methyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

HRID 1035241Notes

Reaction equation

HRID 1035241 reaction equation
[C:1]1([C:7]2[O:11][C:10]([C:12]([N:14]3[CH2:17][CH:16]([O:18][C:19]4[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=4)[CH2:15]3)=[O:13])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.[CH2:34]([C:36]1([OH:40])[CH2:39][NH:38][CH2:37]1)[CH3:35]>>[CH2:34]([C:36]1([OH:40])[CH2:39][N:38]([CH2:23][C:22]2[CH:21]=[CH:20][C:19]([O:18][CH:16]3[CH2:15][N:14]([C:12]([C:10]4[O:11][C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[N:8][N:9]=4)=[O:13])[CH2:17]3)=[CH:26][CH:25]=2)[CH2:37]1)[CH3:35]

Participants

3

Reactant 2

HCID 58043115HCID 58043115, compoundHCID 666534471354792-80-5

Product 1

HCID 56598798(3-(4-((3-Ethyl-3-hydroxyazetidin-1-yl)methyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanoneYield 30%

Procedure

Using a similar protocol as described in Example 70 employing 71A and 70A as starting materials afforded 185 mg (30%) of 71 as a solid. 1H NMR (500 MHz, CDCl3): δ 0.95 (t, 3H), 1.76 (q, 2H), 3.02 (d, 2H), 3.26 (d, 2H), 3.58 (s, 2H), 4.29 (m, 1H), 4.61 (m, 1H), 4.72 (m, 1H), 5.10 (m, 2H), 6.71 (d, 2H), 7.21 (d, 2H), 7.51 (t, 2H), 7.55 (t, 1H), 8.13 (d, 2H), MS (APCI+) m/z 435 [M+H]+, LC purity: 94%.

Sources & evidence

ORD record
ord-c63ce7a927e9451294b309261677ec5b
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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