3-Acetylpyridine → 3-morpholin-4-ylsulfonyl-N-[(E)-1-pyridin-3-ylethylideneamino]benzamide

HRID 877620

反応式

HRID 877620 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([NH:15][NH2:16])=[O:14])(=[O:9])=[O:8])[CH2:3][CH2:2]1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26](=O)[CH3:27])[CH:21]=1>CO.C(O)(=O)C>[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([NH:15]/[N:16]=[C:26](/[C:22]2[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=2)\[CH3:27])=[O:14])(=[O:9])=[O:8])[CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 95893-AcetylpyridineHCID 8772463-(Morpholine-4-sulfonyl)benzohydrazide

生成物 1

HCID 429911443-morpholin-4-ylsulfonyl-N-[(E)-1-pyridin-3-ylethylideneamino]benzamide収率 27.6%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

反応条件

温度
120 °C

実験手順

3-(Morpholinosulfonyl)benzohydrazide (40 mg, 0.140 mmol) and 1-(pyridin-3-yl)ethanone (16.98 mg, 0.140 mmol) were dissolved in methanol (4 mL) in the presence of acetic acid as a catalyst, and the reaction mixture was heated via microwave irradiation to 120° C. for 30 min. The reaction was monitored by TLC. Upon completion of the reaction and following cooling, the solvent was removed by vacuum, and the resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2) affording the title compound as a solid (15 mg). 1H NMR (400 MHz, CDCl3): δ 9.53 (bs, 1H), 8.87 (s, 1H), 8.59 (m, 1H), 8.39 (m, 1H), 8.17 (m, 1H), 7.98 (m, 1H), 7.89 (d, 1H, J=8.0 Hz), 7.67 (t, 1H, J=8.0 Hz), 7.32 (m, 1H), 3.70 (m, 4H), 3.00 (m, 4H), 2.39 (s, 3H). ESI-MS: 389.0 [M+H]+.

後処理

  1. customUpon completion of the reaction
  2. temperaturefollowing cooling
  3. customthe solvent was removed by vacuum
  4. customthe resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2)

出典と根拠

ORDレコード
ord-4f41b56cf5d446ad9333af01237861e7
出典データセット
uspto-grants-2015_03
特許番号
US08987335B2

関連ノート

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