Ethyl 5-(4-(difluoromethoxy)phenyl)-1,3,4-oxadiazole-2-carboxylate → (5-(4-(Difluoromethoxy)phenyl)-1,3,4-oxadiazol-2-yl)(3-(4-((dimethylamino)methyl)phenoxy)azetidin-1-yl)methanone

HRID 1035204Notes

Reaction equation

HRID 1035204 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][N:13]([CH3:15])[CH3:14])=[CH:8][CH:7]=2)[CH2:2]1.[F:16][CH:17]([F:35])[O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:29][C:28]([C:30](OCC)=[O:31])=[N:27][N:26]=2)=[CH:21][CH:20]=1>>[F:35][CH:17]([F:16])[O:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[O:29][C:28]([C:30]([N:1]3[CH2:2][CH:3]([O:5][C:6]4[CH:7]=[CH:8][C:9]([CH2:12][N:13]([CH3:15])[CH3:14])=[CH:10][CH:11]=4)[CH2:4]3)=[O:31])=[N:27][N:26]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 58043152Ethyl 5-(4-(difluoromethoxy)phenyl)-1,3,4-oxadiazole-2-carboxylateHCID 666531201-(4-(Azetidin-3-yloxy)phenyl)-N,N-dimethylmethanamine

Product 1

HCID 56598129(5-(4-(Difluoromethoxy)phenyl)-1,3,4-oxadiazol-2-yl)(3-(4-((dimethylamino)methyl)phenoxy)azetidin-1-yl)methanoneYield 15.2%

Procedure

Using a similar protocol as described in Example 36 employing 33B (0.19 g, 0.92 mmol) and 37A (0.26 g, 0.92 mmol) as starting materials afforded 62 mg (15%) of 37 as a solid. 1H NMR (500 MHz, CDCl3): δ 2.27 (s, 6H), 3.44 (s, 2H), 4.35 (dd, 1H), 4.66 (dd, 1H), 4.77 (dd, 1H), 5.10 (m, 2H), 6.62 (t, 1H), 6.75 (d, 2H), 7.28 (m, 4H), 8.19 (d, 2H), MS (APCI+) m/z 445 [M+H]+, LC purity: 94%.

Sources & evidence

ORD record
ord-34319c8878214f28bbbeb1495f56b669
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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