Ethanamine, 2-(ethylthio)- → N-{[2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methyl}-2-(ethylsulfanyl)ethanamine

HRID 1882058ノート

反応式

HRID 1882058 の反応式
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[S:27][C:28]([CH:31]=O)=[CH:29][N:30]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH2:33]([S:35][CH2:36][CH2:37][NH2:38])[CH3:34].C(=O)([O-])O.[Na+]>C(O)(=O)C.O1CCCC1>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[S:27][C:28]([CH2:31][NH:38][CH2:37][CH2:36][S:35][CH2:33][CH3:34])=[CH:29][N:30]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:11][CH:12]=2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 148011Ethanamine, 2-(ethylthio)-HCID 516892Sodium BicarbonateHCID 593312942-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazole-5-carbaldehyde

生成物 1

HCID 59331289N-{[2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methyl}-2-(ethylsulfanyl)ethanamine

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A mixture of 2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazole-5-carbaldehyde (0.31 g), 2-(ethylsulfanyl)ethanamine (0.14 g), acetic acid (1 drop) and tetrahydrofuran (2 mL) was stirred overnight at 50° C. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was m washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was dissolved in methanol (4 mL), and sodium borohydride (28 mg) was added at 0° C. The reaction mixture was stirred at room temperature for 1 hr, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (0.37 g, quantitatively) was obtained as a yellow oil from a fraction eluted with tetrahydrofuran-hexane (3:1, volume ratio). MS: 471 (MH+).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was m washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. dissolutionThe obtained residue was dissolved in methanol (4 mL)
  6. additionsodium borohydride (28 mg) was added at 0° C
  7. stirringThe reaction mixture was stirred at room temperature for 1 hr
  8. additionwater was added
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with saturated brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-c68b1d6ad2d9472fa762f3e278eee141
出典データセット
uspto-grants-2012_11
特許番号
US08318746B2

反応ノート

読み込み中…