2,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine → 4-(4,6-Dimethylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine

HRID 540277ノート

反応式

HRID 540277 の反応式
Cl[C:2]1[CH:11]=[C:10]([CH2:12]C(O)=O)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:16])[CH:8]=2)[N:3]=1.[S:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][NH:20][CH2:19][CH2:18]1>C(O)CCC.ClCCl>[CH3:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:16])[CH:8]=2)[N:3]=[C:2]([N:20]2[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[S:17][CH2:18][CH2:19]2)[CH:11]=1

参加物

5

反応物 2

HCID 122691062,3,4,5-Tetrahydrobenzo[f][1,4]thiazepineHCID 83647169(2-Chloro-6-methylquinolin-4-yl)acetic acid

生成物 1

HCID 712546364-(4,6-Dimethylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine収率 62.4%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
160 °C

実験手順

A solution of (2-chloro-6-methylquinolin-4-yl)acetic acid (118 mg, 0.5 mmol) and 2,3,4,5-tetrahydro-1,4-benzothiazepine (247 mg, 1.5 mmol) in n-butanol (0.2 mL) was heated with stirring in a sealed 0.5 mL of microwave process vial for 2 hours at 160° C. After being cooled to room temperature, the reaction mixture was diluted with dichloromethane (50 mL), washed with a saturated aqueous solution of sodium carbonate (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (eluting with 20-30% ethyl acetate in petroleum ether) to afford 100 mg of the desired product (yield was 62%). MS (ESI+) [(M+H)+] 321.

後処理

  1. temperatureAfter being cooled to room temperature
  2. washwashed with a saturated aqueous solution of sodium carbonate (50 mL) and brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (eluting with 20-30% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-85587981e3f84897a13338617f0f3969
出典データセット
uspto-grants-2014_10
特許番号
US08871756B2

反応ノート

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