3-Cyclohexene-1-carbonyl chloride → HCID 57004125、化合物

HRID 963259

反応式

HRID 963259 の反応式
[CH3:1][C@@H:2]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH2:3][N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5]1.[CH:22]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][CH:25]=[CH:24][CH2:23]1>C(Cl)Cl>[CH3:1][C@@H:2]([N:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[C:28]([CH:22]1[CH2:27][CH2:26][CH:25]=[CH:24][CH2:23]1)=[O:29])[CH2:3][N:4]1[CH2:5][CH:6]=[C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:8][CH2:9]1

参加物

4

反応物 2

HCID 5230583-Cyclohexene-1-carbonyl chlorideHCID 18660712(R)-[1-Methyl-2-(4-thiophen-2-yl-1,2,3,6-tetrahydropyrid-1-yl)ethyl]-pyrid-2-yl-amine

生成物 1

HCID 57004125HCID 57004125、化合物収率 44.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of the starting (R)-[1-methyl-2-(4-thiophen-2-yl-3,6-dihydro-2H-pyrid-1-yl)-ethyl]-pyrid-2-yl-amine (0.46 g, 1.5 mmol) in methylene chloride (20 ml) was cooled to 0° C., after which a solution of cyclohex-3-enecarbonyl chloride (0.222 g, 1.5 mmol) in methylene chloride (10 ml) was dropwise added under exclusion of moisture. The reaction mixture was stirred at ambient temperature overnight, then washed with 2.5N NaOH (10 ml). The separated organic layer was washed with brine (50 ml), dried over magnesium sulfate, filtered, and evaporated to dryness in vacuo. Column chromatography on 50 g of silica gel with chloroform as eluant, followed by trituration in ether with the addition of ethanolic HCl gave 0.27g of the title compound as the dihydrochloride, m.p. 92°-6° C.

後処理

  1. washwashed with 2.5N NaOH (10 ml)
  2. washThe separated organic layer was washed with brine (50 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo
  6. additionColumn chromatography on 50 g of silica gel with chloroform as eluant, followed by trituration in ether with the addition of ethanolic HCl

出典と根拠

ORDレコード
ord-e997d55740634178bf491cfc3d1247a7
出典データセット
uspto-grants-1998_06
特許番号
US05763460

関連ノート

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