Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 4-(tert-butyldimethylsilyloxy)-2-ethyl-N'-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)cyclopentanecarbohydrazide

HRID 1969916노트

반응식

HRID 1969916 반응식
[Si:1]([O:8][C@H:9]1[CH2:13][C@H:12]([C:14]([OH:16])=O)[C@H:11]([CH2:17][CH3:18])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:19]([C:21]1[N:22]=[C:23]2[CH:29]=[CH:28][N:27]([S:30]([C:33]3[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[C:24]2=[N:25][CH:26]=1)[NH2:20].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.[Si](O[C@H]1C[C@H](C(NNC2N=C3C=CN(S(C4C=CC(C)=CC=4)(=O)=O)C3=NC=2)=O)[C@H](CC)C1)(C(C)(C)C)(C)C>[Si:1]([O:8][CH:9]1[CH2:13][CH:12]([C:14]([NH:20][NH:19][C:21]2[N:22]=[C:23]3[CH:29]=[CH:28][N:27]([S:30]([C:33]4[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=4)(=[O:32])=[O:31])[C:24]3=[N:25][CH:26]=2)=[O:16])[CH:11]([CH2:17][CH3:18])[CH2:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 580098102-Hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazineHCID 67998141(1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-ethylcyclopentanecarboxylic acid

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 67998395(1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-ethyl-N'-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)cyclopentanecarbohydrazide용매

실험 절차

To a scalemic mixture enriched in (1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-ethylcyclopentanecarboxylic acid (1.62 g, 5.96 mmol) in DCM (60 mL) was added 2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (Example #1, Step D, 1.86 g, 6.13 mmol), HATU (2.38 g, 6.26 mmol) and TEA (3.32 mL, 23.8 mmol). The reaction mixture was stirred at ambient temperature for about 1 h. The reaction mixture was diluted with DCM (200 mL), washed with water (50 mL) and brine (50 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The residue was purified using silica gel chromatography eluting with 0-30% EtOAc in DCM to give a scalemic mixture enriched in (1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-ethyl-N′-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)cyclopentanecarbohydrazide (2.64 g, 79%) as a brown solid: LC/MS (Table 1, Method b) Rt=3.20 min; MS m/z: 558 (M+H)+.

후처리

  1. washwashed with water (50 mL) and brine (50 mL)
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. customThe residue was purified
  5. washeluting with 0-30% EtOAc in DCM
  6. customto give a scalemic mixture

출처 및 근거

ORD 기록
ord-ceb78aded3144a6cb2dd689b8417c840
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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