Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate → HCID 56597854, compound

HRID 1035191Notes

Reaction equation

HRID 1035191 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:21]=[CH:20][C:9]([CH2:10][N:11]3[CH2:16][CH2:15][N:14]([C:17](=[O:19])[CH3:18])[CH2:13][CH2:12]3)=[CH:8][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>C1(C)C=CC=CC=1>[C:22]1([C:28]2[O:32][C:31]([C:33]([N:1]3[CH2:2][CH:3]([O:5][C:6]4[CH:21]=[CH:20][C:9]([CH2:10][N:11]5[CH2:12][CH2:13][N:14]([C:17](=[O:19])[CH3:18])[CH2:15][CH2:16]5)=[CH:8][CH:7]=4)[CH2:4]3)=[O:34])=[N:30][N:29]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 651752Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylateHCID 66655835HCID 66655835, compound

Product 1

HCID 56597854HCID 56597854, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

23B (0.16 g, 0.53 mmol) and ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.11 g, 0.50 mmol) were mixed together in a microwave vial together with toluene (3 mL). The mixture was heated in a microwave oven at 140° C. for 30 min. The solvent was removed by evaporation. The product was purified by preparative chromatography on a Kromasil C8 column eluting with acetonitrile and 0.1 M NH4OAc. The combined fractions were concentrated and the aqueous solution was pH adjusted to pH 9 with 1M NaOH. The mixture was extracted with EtOAc and the organic layer was dried over Na2SO4. The solvent was removed by evaporation. There was obtained 24 mg (10%) of the product as a foam. 1H NMR (400 MHz, CDCl3): δ 2.08 (s, 3H), 2.32-2.47 (m, 4H), 3.37-3.54 (m, 4H), 3.62 (s, 2H), 4.29-4.40 (m, 1H), 4.59-4.70 (m, 1H), 4.71-4.82 (m, 1H), 5.02-5.19 (m, 2H), 6.74 (d, 2H), 7.26 (d, 2H), 7.49-7.64 (m, 3H), 8.16 (d, 2H), MS (APCI+) m/z 462 [M+H]+, LC purity: 93%.

Workup

  1. customThe solvent was removed by evaporation
  2. customThe product was purified by preparative chromatography on a Kromasil C8 column
  3. washeluting with acetonitrile and 0.1 M NH4OAc
  4. concentrationThe combined fractions were concentrated
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialthe organic layer was dried over Na2SO4
  7. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-8d8f2fd5c42b4c7e8f7043bdd493b435
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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