3,5-Dichlorobenzoyl chloride → N-(2-(benzo[d]isothiazol-3-ylamino)ethyl)-1-(3,5-dichlorobenzoyl)piperidine-3-carboxamide

HRID 502546ノート

反応式

HRID 502546 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][CH2:11][CH2:12][NH:13][C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[O:15])=[N:2]1.C(N(C(C)C)CC)(C)C.[Cl:31][C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([Cl:41])[CH:40]=1)[C:35](Cl)=[O:36]>ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][CH2:11][CH2:12][NH:13][C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:35](=[O:36])[C:34]3[CH:33]=[C:32]([Cl:31])[CH:40]=[C:39]([Cl:41])[CH:38]=3)[CH2:17]2)=[O:15])=[N:2]1

参加物

5

反応物 3

HCID 761913,5-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 11856088N-(2-(benzo[d]isothiazol-3-ylamino)ethyl)piperidine-3-carboxamide

生成物 1

HCID 57436314N-(2-(benzo[d]isothiazol-3-ylamino)ethyl)-1-(3,5-dichlorobenzoyl)piperidine-3-carboxamide収率 20.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

N-(2-(Benzo[d]isothiazol-3-ylamino)ethyl)piperidine-3-carboxamide (75 mg, 0.24 mmol) was dissolved in anhydrous dichloromethane (5 mL) with diisopropylethylamine (38 μL, 0.27 mmol). The solution was cooled on an ice-water bath and then a solution of 3,5-dichlorobenzoyl chloride (57 mg, 0.27 mmol) in dichloromethane (0.5 mL) was added dropwise. The reaction mixture was allowed to stir overnight while warming to room temperature. The solution was washed with saturated sodium bicarbonate solution and brine, then dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under reduced pressure. Purification by column chromatography, on silica gel, eluting with a mixture of 25% ethyl acetate in hexanes and selected fractions were combined and concentrated under reduced pressure to yield N-(2-(benzo[d]isothiazol-3-ylamino)ethyl)-1-(3,5-dichlorobenzoyl)piperidine-3-carboxamide (23 mg). 1H NMR (300 MHz, CDCl3): 7.8 (m, 1H), 7.5 (m, 1H), 7.3 (m, 2H), 7.1 (m, 1H), 6.3 (m, 1H), 3.7 (m, 4H), 3.3 (m, 2H), 2.5 (m, 1H), 1.8 (m, 1H), 1.6 (m, 3H) 1.1 ppm (m, 1H). MW=477 confirmed by LC-MS, tr=3.93 min (Method Y) MH+=478.

後処理

  1. temperatureThe solution was cooled on an ice-water bath
  2. washThe solution was washed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customPurification by column chromatography
  7. washon silica gel, eluting with a mixture of 25% ethyl acetate in hexanes
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-1d995d527e654189bcc89ccd083edfa5
出典データセット
uspto-grants-2010_08
特許番号
US07776847B2

反応ノート

読み込み中…