Ethyl Acetate → tert-butyl 1-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)pyrrolidin-3-ylcarbamate

HRID 1969533

반응식

HRID 1969533 반응식
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH2:20][NH:21][C:22]([N:24]3[CH2:28][CH2:27][CH:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25]3)=S)[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+].CCOC(C)=O>C1COCC1.FC(F)(F)C([O-])=O.[Hg+2].FC(F)(F)C([O-])=O>[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:22]([N:24]4[CH2:28][CH2:27][CH:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25]4)=[N:21][CH:20]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 58558007tert-butyl 1-((5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methylcarbamothioyl)pyrrolidin-3-ylcarbamate

생성물 1

HCID 67998161tert-butyl 1-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)pyrrolidin-3-ylcarbamate수율 82.8%

시약·촉매·용매 2

HCID 2723924Mercury bis(trifluoroacetate)촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl 1-((5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methylcarbamothioyl)-pyrrolidin-3-ylcarbamate (0.54 g, 1.0 mmol, Preparation #J.1) in THF (15 mL) was added DIEA (0.444 mL, 2.54 mmol) followed by mercury (II) trifluoroacetate (0.478 g, 1.12 mmol). The reaction mixture was stirred at ambient temperature for about 2 h and then saturated aqueous NaHCO3 (30 mL) and EtOAc (30 mL) were added. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concd in vacuo. The crude material was purified by chromatography on silica gel (40 g) eluting with 10-40% EtOAc in DCM to provide tert-butyl 1-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)pyrrolidin-3-ylcarbamate (0.411 g, 81%) as a yellow glass: LC/MS (Table 1, Method a) Rt=2.50 min; MS m/z: 497 (M+H)+.

후처리

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customThe crude material was purified by chromatography on silica gel (40 g)
  5. washeluting with 10-40% EtOAc in DCM

출처 및 근거

ORD 기록
ord-cd15607c98984245835ec91f8b2d50cc
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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