Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate → (5-Phenyl-1,3,4-oxadiazol-2-yl)(3-(4-(pyrrolidin-1-ylmethyl)-3-(trifluoromethyl)phenoxy)azetidin-1-yl)methanone

HRID 1035209Notes

Reaction equation

HRID 1035209 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:17]=[CH:16][C:9]([CH2:10][N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[C:8]([C:18]([F:21])([F:20])[F:19])[CH:7]=2)[CH2:2]1.[C:22]1([C:28]2[O:32][C:31]([C:33](OCC)=[O:34])=[N:30][N:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:22]1([C:28]2[O:32][C:31]([C:33]([N:1]3[CH2:4][CH:3]([O:5][C:6]4[CH:17]=[CH:16][C:9]([CH2:10][N:11]5[CH2:12][CH2:13][CH2:14][CH2:15]5)=[C:8]([C:18]([F:19])([F:20])[F:21])[CH:7]=4)[CH2:2]3)=[O:34])=[N:30][N:29]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 651752Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylateHCID 666532771-(4-(Azetidin-3-yloxy)-2-(trifluoromethyl)benzyl)pyrrolidine

Product 1

HCID 56598398(5-Phenyl-1,3,4-oxadiazol-2-yl)(3-(4-(pyrrolidin-1-ylmethyl)-3-(trifluoromethyl)phenoxy)azetidin-1-yl)methanoneYield 77%

Procedure

Using a similar protocol as described in Example 16 employing 45A (0.19 g, 0.65 mmol) and ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.15 g, 0.71 mmol) as starting materials afforded 230 mg (77%) of 45 as a solid. 1H NMR (500 MHz, CDCl3): δ 1.81 (s, 4H), 2.55 (s, 4H), 3.74 (s, 2H), 4.35 (dd, 1H), 4.67 (dd, 1H), 4.78 (dd, 1H), 5.14 (m, 2H), 6.93 (d, 1H), 7.05 (d, 1H), 7.54 (t, 2H), 7.60 (t, 1H), 7.73 (d, 1H), 8.17 (d, 2H), MS (APCI+) m/z 473 [M+H]+, LC purity: 97%.

Sources & evidence

ORD record
ord-6306331008c84e868b88d3fff74311f0
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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