4-Benzyloxybenzoylchloride → 3-(4-(5-(4-(Benzyloxy)phenyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyridine

HRID 2167339

Reaction equation

HRID 2167339 reaction equation
[OH:1]/[N:2]=[C:3](\[NH2:17])/[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:6][CH:5]=1.CN(C)N1C=CC=CC1.[CH2:27]([O:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=O)=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>N1C=CC=CC=1>[CH2:27]([O:34][C:35]1[CH:36]=[CH:37][C:38]([C:39]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[CH:6][C:7]([O:10][C:11]4[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=4)=[CH:8][CH:9]=3)[N:17]=2)=[CH:42][CH:43]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 37664104-BenzyloxybenzoylchlorideHCID 6453552N,N-dimethylpyridin-1-amineHCID 43144888HCID 43144888, compound

Product 1

HCID 595339523-(4-(5-(4-(Benzyloxy)phenyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyridineYield 79.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(Z)-N′-Hydroxy-4-(pyridin-3-yloxy)benzamidine (206 mg, 89.9 μmol), N-dimethylaminopyridine (1.1 mg, 9.0 μmol) and 4-benzyloxybenzoyl chloride (28.8 mg, 116.8 μmol) were suspended in pyridine (5.0 mL) and the solution was refluxed for 45 hours. The reaction mixture was then cooled to room temperature, the solvent was removed under reduced pressure and the solid residue was purified by column chromatography (EtOAc/Hex 1:4) to give the product as a white solid (30 mg, 78%). 1H NMR (500 MHz, CDCL3) δ(ppm): 5.16 (2H, s), 7.11 (2H, d, J=6.0 Hz), 7.12 (2H, d, J=6.2 Hz), 7.33-7.37 (2H, m), 7.39-7.46 (5H, m), 8.15 (2H, d, J=7.6 Hz), 8.17 (2H, d, J=7.4 Hz), 8.45 (1H, d, J=4.6 Hz), 8.49 (1H, d, J=2.4 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 70.4 (CH2), 115.5 (CH), 117.2, 118.8 (CH), 123.0 (CH), 124.6, 126.8 (CH), 127.7 (CH), 128.5 (CH), 128.8, 128.9 (CH), 129.7 (CH), 130.3 (CH), 136.2, 141.9, 145.0, 159.1, 162.5, 168.3, 175.8. MS (FAB+): 422 (MH+). HRMS for C26H19N3O3 (MH+): calculated: 422.1505; found 422.1521.

Workup

  1. temperaturethe solution was refluxed for 45 hours
  2. customthe solvent was removed under reduced pressure
  3. customthe solid residue was purified by column chromatography (EtOAc/Hex 1:4)

Sources & evidence

ORD record
ord-31307564b39547ce93698ca32e6de08a
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Linked notes

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