2-Bromo-N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]acetamide → N-[4-(2-Furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]-2-[(7S,8aS)-7-hydroxyoctahydropyrrolo[1,2-a]pyrazin-2-yl]acetamide

HRID 1361867노트

반응식

HRID 1361867 반응식
Br[CH2:2][C:3]([NH:5][C:6]1[S:7][C:8]([C:16]([CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[O:17])=[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)=[O:4].O1CCCCC1[O:30][C@@H:31]1[CH2:39][N:34]2[CH2:35][CH2:36][NH:37][CH2:38][C@@H:33]2[CH2:32]1>C1COCC1>[O:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:9]1[N:10]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:37]2[CH2:36][CH2:35][N:34]3[CH2:39][C@@H:31]([OH:30])[CH2:32][C@H:33]3[CH2:38]2)[S:7][C:8]=1[C:16]([CH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:17]

참가 물질

4

반응물 2

HCID 231445052-Bromo-N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]acetamideHCID 66968036(7S,8aS)-7-(tetrahydropyran-2-yl)oxyoctahydropyrrolo[1,2-a]pyrazine

생성물 1

HCID 86612470N-[4-(2-Furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]-2-[(7S,8aS)-7-hydroxyoctahydropyrrolo[1,2-a]pyrazin-2-yl]acetamide수율 34%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Compound 531 (120 mg, 0.300 mmol) was dissolved in THF (2 mL), and (7S,8aS)-7-(tetrahydropyran-2-yl)oxyoctahydropyrrolo[1,2-a]pyrazine (204 mg, 0.900 mmol) was added thereto, followed by stirring at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was dissolved in ethanol (3 mL), and 2 mol/L hydrochloric acid (3 mL) was added thereto, followed by stirring overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the resulting residue was poured into water. A 2 mol/L sodium hydroxide solution added thereto to adjust the pH to 8, followed by extraction with chloroform. The organic layer was washed with a solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=23:2), followed by recrystallizing from a mixed solvent of ethanol and diethyl ether to afford the entitled Compound 569 (46.5 mg, 34%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in ethanol (3 mL)
  3. addition2 mol/L hydrochloric acid (3 mL) was added
  4. stirringby stirring overnight at room temperature
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. additionthe resulting residue was poured into water
  7. additionA 2 mol/L sodium hydroxide solution added
  8. extractionfollowed by extraction with chloroform
  9. washThe organic layer was washed with a solution of sodium chloride
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled away under reduced pressure
  12. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=23:2)
  13. customby recrystallizing from a mixed solvent of ethanol and diethyl ether

출처 및 근거

ORD 기록
ord-90c4997dd3d94df98fcfd43ce0d0b0e8
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07880013B2

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