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

HRID 1035203Notes

Reaction equation

HRID 1035203 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.[C:16]1([C:22]2[O:26][C:25]([C:27](OCC)=[O:28])=[N:24][N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH3:14][N:13]([CH2:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH:3]2[CH2:2][N:1]([C:27]([C:25]3[O:26][C:22]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[N:23][N:24]=3)=[O:28])[CH2:4]2)=[CH:11][CH:10]=1)[CH3:15]

Participants

3

Reactant 2

HCID 651752Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylateHCID 666531201-(4-(Azetidin-3-yloxy)phenyl)-N,N-dimethylmethanamine

Product 1

HCID 56598126(3-(4-((Dimethylamino)methyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanoneYield 38%

Procedure

Using a similar protocol as described in Example 16 employing 33B (0.10 g, 0.48 mmol) and ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.12 g, 0.53 mmol) as starting materials afforded 69 mg (38%) of 33 as a solid. 1H NMR (500 MHz, CDCl3): δ 2.24 (s, 6H), 3.37 (s, 2H), 4.34 (dd, 1H), 4.65 (dd, 1H), 4.77 (dd, 1H), 5.10 (m, 2H), 6.74 (d, 2H), 7.24 (m, 2H), 7.55 (m, 3H), 8.15 (d, 2H), MS (APCI+) m/z 379 [M+H]+, LC purity: 95%.

Sources & evidence

ORD record
ord-549298f641eb4277acf043f944c78e6b
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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