Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate → HCID 56597689, compound

HRID 1035181Notes

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

Participants

Conditions

Temperature: 120 °C

Procedure

Intermediate 16B (0.25 g, 1.13 mmol) was mixed with ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.27 g, 1.25 mmol) in a microwave vial, which then was sealed. The mixture was melted in a preheated oil bath and then stirred at 120° C. for 15 min using the oil bath. EtOH (0.2 mL) was added to the reaction mixture via a syringe and the mixture was stirred at 120° C. for another 3 h. To the mixture was added EtOH (5 mL) and the precipitate was stirred at rt for 20 min. The precipitate was filtered, washed with EtOH (20 mL) and then with Et2O (3 mL). The product was dried in vacuo. There was obtained 0.26 g (57%) of 16 as a solid. 1H NMR (500 MHz, CDCl3): δ 2.23 (s, 6H), 2.35 (s, 3H), 3.32 (s, 2H), 4.29-4.37 (m, 1H), 4.60-4.69 (m, 1H), 4.71-4.79 (m, 1H), 5.02-5.17 (m, 2H), 6.52-6.57 (m, 1H), 6.61 (s, 1H), 7.17 (d, 1H), 7.50-7.62 (m, 3H), 8.17 (d, 2H), MS (APCI+) m/z 393 [M+H]+, LC purity: 98%.

Workup

customthen was sealed
customThe mixture was melted in a preheated oil bath
stirringthe mixture was stirred at 120° C. for another 3 h
stirringthe precipitate was stirred at rt for 20 min
filtrationThe precipitate was filtered
washwashed with EtOH (20 mL)
customThe product was dried in vacuo

Sources & evidence

ORD record: ord-cbb6396abd3a4f97b1e29895674b97e0
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546375B2

Reaction notes

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