Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate → 4-[2-Methoxy-4-({1-[(5-phenyl-1,3,4-oxadiazol-2-yl)carbonyl]azetidin-3-yl}oxy)benzyl]morpholine

HRID 1035172Notes

Reaction equation

[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:18]=[CH:17][C:9]([CH2:10][N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[C:8]([O:19][CH3:20])[CH:7]=2)[CH2:2]1.[C:21]1([C:27]2[O:31][C:30]([C:32](OCC)=[O:33])=[N:29][N:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCO>[CH3:20][O:19][C:8]1[CH:7]=[C:6]([O:5][CH:3]2[CH2:4][N:1]([C:32]([C:30]3[O:31][C:27]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[N:28][N:29]=3)=[O:33])[CH2:2]2)[CH:18]=[CH:17][C:9]=1[CH2:10][N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 7C (0.25 g, 0.90 mmol), ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.22 g, 1.00 mmol) and EtOH (2 mL) was heated in a microwave oven at 120° C. for 60 min. The mixture was left over-night at RT. The formed precipitate was isolated by filtration and then washed with EtOH. There was obtained 0.18 g (45%) of 7 as a solid. 1H NMR (500 MHz, CDCl3): δ 2.33-2.66 (m, 4H), 3.50 (s, 2H), 3.65-3.78 (m, 4H), 3.81 (s, 3H), 4.29-4.39 (m, 1H), 4.59-4.70 (m, 1H), 4.72-4.80 (m, 1H), 5.02-5.19 (m, 2H), 6.25 (d, 1H), 6.42 (s, 1H), 7.26 (s, 1H), 7.50-7.63 (m, 3H), 8.13-8.20 (m, 2H), MS (APCI+) m/z 451 [M+H]+, LC purity: 99%.

Workup

waitThe mixture was left over-night at RT
customThe formed precipitate was isolated by filtration
washwashed with EtOH

Sources & evidence

ORD record: ord-b51a56b355b94ea89cc2d9147a87d6dc
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546375B2

Reaction notes

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