Water → 3-[6-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridin-2-yl]-4,5-dihydro-1,2,4-thiadiazol-5-one

HRID 2400300ノート

反応式

HRID 2400300 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[N:18]=[C:17]([C:19](=[N:21]O)[NH2:20])[CH:16]=[CH:15][CH:14]=1)[C:7]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:6]2.[C:29](N1C=CN=C1)(N1C=CN=C1)=[S:30].[OH2:41]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[N:18]=[C:17]([C:19]3[NH:20][C:29](=[O:41])[S:30][N:21]=3)[CH:16]=[CH:15][CH:14]=1)[C:7]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:6]2

参加物

5

反応物 3

HCID 962WaterHCID 802641,1'-ThiocarbonyldiimidazoleHCID 1363380916-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxamidoxime

生成物 1

HCID 1363380943-[6-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridin-2-yl]-4,5-dihydro-1,2,4-thiadiazol-5-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxamidoxime (123 mg) in tetrahydrofuran (2 mL) was added 1,1′-thiocarbonyldiimidazole (71 mg). This mixture was stirred at room temperature for 1 hour. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the residue was added tetrahydrofuran (2 mL), and subsequently boron trifluoride ethyl ether complex (0.21 mL) was added thereto under ice-cooling. The mixture was stirred at room temperature for 3 days. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid and water successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol) to obtain the title compound (24 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 5.55 (2H, s), 6.45-6.55 (1H, m), 6.60-6.70 (1H, m), 6.77 (1H, dd, J=2.5, 8.9 Hz), 7.14 (1H, d, J=2.5 Hz), 7.28 (1H, d, J=8.9 Hz), 7.35-7.60 (5H, m), 7.75-7.95 (2H, m), 13.35 (1H, br s). ESI-MS (m/z): 415 (M+H)+

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added tetrahydrofuran (2 mL), and subsequently boron trifluoride ethyl ether complex (0.21 mL)
  6. additionwas added
  7. temperatureunder ice-cooling
  8. stirringThe mixture was stirred at room temperature for 3 days
  9. additionTo the reaction mixture was added water
  10. extractionfollowed by extraction with ethyl acetate
  11. washThe organic layer was washed with 1 mol/L hydrochloric acid and water successively
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol)

出典と根拠

ORDレコード
ord-2c4f2dfc0514463e88c4398ea56dd822
出典データセット
uspto-grants-2014_08
特許番号
US08796247B2

反応ノート

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