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

HRID 1035201Notes

Reaction equation

HRID 1035201 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]([F:18])[CH:7]=2)[CH2:2]1.[C:19]1([C:25]2[O:29][C:28]([C:30](OCC)=[O:31])=[N:27][N:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[F:18][C:8]1[CH:7]=[C:6]([CH:17]=[CH:16][C:9]=1[CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[O:5][CH:3]1[CH2:4][N:1]([C:30]([C:28]2[O:29][C:25]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[N:26][N:27]=2)=[O:31])[CH2:2]1

Participants

3

Reactant 2

HCID 651752Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylateHCID 66653359HCID 66653359, compound

Product 1

HCID 56598125(3-(3-Fluoro-4-(pyrrolidin-1-ylmethyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanoneYield 71%

Procedure

Using a similar protocol as described in Example 16 employing 31C (0.11 g, 0.44 mmol) and ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.10 g, 0.48 mmol) as starting materials afforded 130 mg (71%) of 31 as a solid. 1H NMR (500 MHz, CDCl3): δ 1.80 (s, 4H), 2.50 (s, 4H), 3.65 (s, 2H), 4.30 (m, 1H), 4.65 (m, 1H), 4.75 (m, 1H), 5.05 (m, 1H), 5.15 (m, 1H), 6.50 (m, 2H), 7.30 (t, 1H), 7.55 (m, 3H), 8.20 (d, 2H), MS (APCI+) m/z 423 [M+H]+, LC purity: 95%.

Sources & evidence

ORD record
ord-051fccbe00b749e580e475d2ae75b1f3
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

Loading…