Ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate → HCID 56598531, compound

HRID 1035227Notes

Reaction equation

HRID 1035227 reaction equation
[NH:1]1[CH2:4][CH:3]([S:5][C:6]2[CH:17]=[CH:16][C:9]([CH2:10][N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[CH:8][CH:7]=2)[CH2:2]1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:30][C:29]([C:31](OCC)=[O:32])=[N:28][N:27]=2)=[CH:22][CH:21]=1>>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[O:30][C:29]([C:31]([N:1]3[CH2:2][CH:3]([S:5][C:6]4[CH:17]=[CH:16][C:9]([CH2:10][N:11]5[CH2:12][CH2:13][CH2:14][CH2:15]5)=[CH:8][CH:7]=4)[CH2:4]3)=[O:32])=[N:28][N:27]=2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 13407471Ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylateHCID 66653518HCID 66653518, compound

Product 1

HCID 56598531HCID 56598531, compoundYield 24%

Conditions

Temperature
120 °C

Procedure

Intermediate 59E (0.37 g, 1.5 mmol) and ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate (0.48 g, 1.9 mmol) were mixed and heated to 120° C. for 2 h using an oil-bath. The product was purified by flash-chromatography using 1-5% methanol/DCM where the methanol contained ammonia (2M). The product crystallised when adding ether and the solid was dried in vacuo. There was obtained 0.16 g (24%) of 59 as a solid. 1H NMR (500 MHz, CDCl3): δ 1.81 (m, 4H), 2.51 (m, 4H), 3.62 (m, 2H), 3.89 (s, 3H), 4.18 (m, 2H), 4.63 (m, 2H), 5.11 (m, 1H), 7.02 (d, 2H), 7.27 (m, 4H), 8.09 (d, 2H), MS (APCI+) m/z 451 [M+H]+, LC purity: 97%.

Workup

  1. customThe product was purified by flash-chromatography
  2. customThe product crystallised when
  3. additionadding ether
  4. customthe solid was dried in vacuo

Sources & evidence

ORD record
ord-e83d9a411f5a44cc8434ea101b9f4b0c
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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