Imidazole → 4-(tert-butyldimethylsilyloxy)-2-ethyl-N'-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)cyclopentanecarbohydrazide

HRID 1969927노트

반응식

HRID 1969927 반응식
C([C@@H]1C[C@H](O)C[C@@H]1C(N(C1N=C2C=CN(S(C3C=CC(C)=CC=3)(=O)=O)C2=NC=1)N)=O)C.CC([Si](Cl)(C)C)(C)C.N1C=CN=C1.[Si:45]([O:52][C@@H:53]1[CH2:57][C@H:56]([C:58]([NH:60][NH:61][C:62]2[N:63]=[C:64]3[CH:70]=[CH:69][N:68]([S:71]([C:74]4[CH:80]=[CH:79][C:77]([CH3:78])=[CH:76][CH:75]=4)(=[O:73])=[O:72])[C:65]3=[N:66][CH:67]=2)=[O:59])[C@H:55]([CH2:81][CH3:82])[CH2:54]1)([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46]>CN(C=O)C>[Si:45]([O:52][CH:53]1[CH2:57][CH:56]([C:58]([NH:60][NH:61][C:62]2[N:63]=[C:64]3[CH:70]=[CH:69][N:68]([S:71]([C:74]4[CH:75]=[CH:76][C:77]([CH3:78])=[CH:79][CH:80]=4)(=[O:73])=[O:72])[C:65]3=[N:66][CH:67]=2)=[O:59])[CH:55]([CH2:81][CH3:82])[CH2:54]1)([C:48]([CH3:49])([CH3:50])[CH3:51])([CH3:46])[CH3:47]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67998348(1S,2R,4S)-2-ethyl-4-hydroxy-N-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)cyclopentanecarbohydrazideHCID 67998401(1S,2R,4S)-4-(tert-butyldimethylsilyloxy)-2-ethyl-N'-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)cyclopentanecarbohydrazide

생성물 1

HCID 585573274-(tert-butyldimethylsilyloxy)-2-ethyl-N'-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)cyclopentanecarbohydrazide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a scalemic mixture enriched in (1S,2R,4S)-2-ethyl-4-hydroxy-N-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)cyclopentanecarbo-hydrazide (9.06 g, 20.43 mmol) in DMF (40.9 mL) was added TBDMSCl (3.69 g, 24.51 mmol) and imidazole (3.48 g, 51.1 mmol). The reaction mixture was stirred at ambient temperature for about 4 h. The solvent was removed under reduced pressure. The residue was diluted with EtOAc (200 mL), filtered, and washed with EtOAc (20 mL). The filtrate was concd under reduced pressure. The residue was purified using silica gel chromatography eluting with 0-50% EtOAc in DCM to give a scalemic mixture enriched in (1S,2R,4S)-4-(tert-butyldimethylsilyloxy)-2-ethyl-N′-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)cyclopentanecarbohydrazide (11.37 g, 100%) as an orange solid: LC/MS (Table 1, Method b) Rt=3.14 min; MS m/z: 558 (M+H)+.

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with EtOAc (200 mL)
  3. filtrationfiltered
  4. washwashed with EtOAc (20 mL)
  5. customThe residue was purified
  6. washeluting with 0-50% EtOAc in DCM
  7. customto give a scalemic mixture

출처 및 근거

ORD 기록
ord-15ca97b524bc4a518fac5e4b70bcc50f
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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