Tetrahydrofuran → Methyl 4-[5-(2,2'-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-3-methoxybenzoate

HRID 219928Notes

Reaction equation

HRID 219928 reaction equation
[NH2:1][C:2](=[N:15][OH:16])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14].CCN([CH:23]([CH3:25])[CH3:24])C(C)C.[CH2:26]1[CH2:30]O[CH2:28][CH2:27]1>O>[CH3:28][C:27]1[CH:2]=[C:3]([C:12]2[O:16][N:15]=[C:2]([C:3]3[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=3[O:13][CH3:14])[N:1]=2)[CH:4]=[CH:5][C:26]=1[C:30]1[CH:11]=[CH:6][CH:7]=[CH:25][C:23]=1[CH3:24]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 72307497Methyl 4-[amino(hydroxyimino)methyl]-3-methoxybenzoate

Product 1

HCID 67529208Methyl 4-[5-(2,2'-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

The title compound was prepared following procedure described for example 43, step 1 to give 2,2′-dimethylbiphenyl-4-carbonyl chloride (0.50 mmol) as a yellow oil. The latter was dissolved in anhydrous THF (3 mL), Intermediate 47 (112.11 mg; 0.50 mmol) and DIEA (170.06 μL; 1 mmol) were added under argon. The mixture was heated in the microwave at 150° C. for 15 min. The reaction mixture was diluted in water and extracted with EtOAc, the organic phase was then washed with NH4Cl, NaHCO3 and NaCl sat. solution. The organic layer was then dried over magnesium sulfate, filtered and concentrated, the crude product was suspended in ACN, filtrated, recristalized in EtOAC and dried under vacuo, affording the title compound as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.15-8.12 (m, 2H), 8.06 (dd, J=7.6, 1.5 Hz, 1H), 7.77-7.72 (m, 2H), 7.38-7.27 (m, 4H), 7.14-7.11 (m, 1H), 4 (s, 3H), 3.92 (s, 3H), 2.13 (s, 3H), 2.03 (s, 3H). LC/MS (Method A): 415.3 (M+H)+. HPLC (Method A) Rt 6 min (Purity: 98.1%).

Workup

  1. extractionextracted with EtOAc
  2. washthe organic phase was then washed with NH4Cl, NaHCO3 and NaCl sat. solution
  3. dry with materialThe organic layer was then dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationfiltrated
  7. customdried under vacuo

Sources & evidence

ORD record
ord-b2802938b7a94c92b1bcb85765c2a1f6
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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