4-Benzyloxybenzoylchloride → HCID 59533952、化合物

HRID 2167339

反応式

HRID 2167339 の反応式
[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

参加物

5

反応物 3

HCID 37664104-BenzyloxybenzoylchlorideHCID 6453552N,N-dimethylpyridin-1-amineHCID 43144888HCID 43144888、化合物

生成物 1

HCID 59533952HCID 59533952、化合物収率 79.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-31307564b39547ce93698ca32e6de08a
出典データセット
uspto-grants-2015_06
特許番号
US09045442B2

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