Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → N,N-diethyl-1-(3-ethyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentyl)methanesulfonamide

HRID 1969702노트

반응식

HRID 1969702 반응식
[NH:1]([C:3]1[N:4]=[C:5]2[CH:11]=[CH:10][N:9]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]2=[N:7][CH:8]=1)[NH2:2].[CH2:22]([N:24]([CH2:39][CH3:40])[S:25]([CH2:28][CH:29]1[CH2:33][CH:32]([C:34](O)=[O:35])[CH:31]([CH2:37][CH3:38])[CH2:30]1)(=[O:27])=[O:26])[CH3:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:39]([N:24]([CH2:22][CH3:23])[S:25]([CH2:28][CH:29]1[CH2:33][CH:32]([C:34]([NH:2][NH:1][C:3]2[N:4]=[C:5]3[CH:11]=[CH:10][N:9]([S:12]([C:15]4[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=4)(=[O:13])=[O:14])[C:6]3=[N:7][CH:8]=2)=[O:35])[CH:31]([CH2:37][CH3:38])[CH2:30]1)(=[O:27])=[O:26])[CH3:40]

참가 물질

5

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 585578104-((N,N-diethylsulfamoyl)methyl)-2-ethylcyclopentanecarboxylic acid

생성물 1

HCID 58557160N,N-diethyl-1-(3-ethyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentyl)methanesulfonamide수율 98.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (0.390 g, 1.287 mmol, Example #1 Step D), 4-((N,N-diethylsulfamoyl)methyl)-2-ethylcyclopentanecarboxylic acid (0.375 g, 1.287 mmol), and HATU (0.538 g, 1.416 mmol) in DCM (6.4 mL) was added TEA (0.538 mL, 3.86 mmol). The reaction mixture was stirred at ambient temperature for about 1 h. The reaction mixture was partitioned between water (50 mL) and DCM (50 mL). The aqueous layer was extracted with DCM (2×50 mL). The organic layers were combined and concd under reduced pressure. The material was purified by silica gel (120 g) chromatography eluting with a gradient of 20-100% EtOAc in DCM to provide N,N-diethyl-1-(3-ethyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentyl)methanesulfonamide (0.730 g, 98%) as a brown solid: LC/MS (Table 1, Method b) Rt=2.39 min; MS m/z: 577 (M+H)+.

후처리

  1. customThe reaction mixture was partitioned between water (50 mL) and DCM (50 mL)
  2. extractionThe aqueous layer was extracted with DCM (2×50 mL)
  3. customThe material was purified by silica gel (120 g) chromatography
  4. washeluting with a gradient of 20-100% EtOAc in DCM

출처 및 근거

ORD 기록
ord-8f82224280bb4dd0818c7a53b32b2733
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

반응 노트

불러오는 중…