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

HRID 1969927ノート

反応式

HRID 1969927 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-15ca97b524bc4a518fac5e4b70bcc50f
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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