4-Toluenesulfonyl chloride → N-((1S,3R,4S)-3-ethyl-4-(5-nitro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)cyclopentyl)cyclopropanesulfonamide

HRID 1969817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969817
[CH2:1]([C@H:3]1[C@@H:7]([NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][N:12]=[C:11]3[NH:18][CH:19]=[CH:20][C:10]=23)[CH2:6][C@@H:5]([NH:21][S:22]([CH:25]2[CH2:27][CH2:26]2)(=[O:24])=[O:23])[CH2:4]1)[CH3:2].[H-].[Na+].[CH3:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>CN(C=O)C.CCOC(C)=O>[CH2:1]([C@H:3]1[C@@H:7]([NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][N:12]=[C:11]3[N:18]([S:37]([C:34]4[CH:35]=[CH:36][C:31]([CH3:30])=[CH:32][CH:33]=4)(=[O:39])=[O:38])[CH:19]=[CH:20][C:10]=23)[CH2:6][C@@H:5]([NH:21][S:22]([CH:25]2[CH2:27][CH2:26]2)(=[O:24])=[O:23])[CH2:4]1)[CH3:2]

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chloride2×HCID 24758Sodium hydride3×HCID 67999320N-((1S,3R,4S)-3-ethyl-4-(5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)cyclopentyl)cyclopropanesulfonamide

Produkt 1

HCID 67998126N-((1S,3R,4S)-3-ethyl-4-(5-nitro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)cyclopentyl)cyclopropanesulfonamideAusbeute 126,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-((1S,3R,4S)-3-ethyl-4-(5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)cyclopentyl)cyclopropanesulfonamide (0.123 g, 0.314 mmol) in DMF (3.0 mL) at about 0° C. was added NaH (60% in mineral oil, 0.015 g, 0.37 mmol). The reaction mixture was stirred for about 5 min. 4-Methylbenzene-1-sulfonyl chloride (0.060 g, 0.314 mmol) was added and the reaction mixture was stirred for about 30 min. Additional NaH (60% in mineral oil, 0.007 g, 0.18 mmol) was added and the reaction mixture was stirred for about 10 min. Additional NaH (60% in mineral oil, 0.005 g, 0.12 mmol) was added and the reaction mixture was stirred for about 15 min. Additional 4-methylbenzene-1-sulfonyl chloride (0.012 g, 0.063 mmol) was added and the reaction mixture was stirred for about 40 min. The reaction mixture was concd under reduced pressure. The residue was dissolved in EtOAc (25 mL) and washed with water (15 mL). The organic layer was separated, dried over anhydrous MgSO4, filtered and concd under reduced pressure to give N-((1S,3R,4S)-3-ethyl-4-(5-nitro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)cyclopentyl)-cyclopropanesulfonamide (0.218 g) as a red-orange oil containing 40 mol % DMF and 1 equivalent EtOAc: LC/MS (Table 1, Method n) Rt=0.88 min; MS m/z 548 (M+H)+.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for about 30 min
  2. stirringthe reaction mixture was stirred for about 10 min
  3. stirringthe reaction mixture was stirred for about 15 min
  4. stirringthe reaction mixture was stirred for about 40 min
  5. washwashed with water (15 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-09cefd3a99b74411812f6037003d18a1
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

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