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

HRID 1969927Notes

Reaction equation

HRID 1969927 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-15ca97b524bc4a518fac5e4b70bcc50f
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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