1-Propanesulfonyl chloride → N-{1-benzenesulfonyl-4-[1-(propane-1-sulfonyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-2-cyano-acetamide

HRID 1257600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257600
C(N(C(C)C)CC)(C)C.[CH2:10]([S:13](Cl)(=[O:15])=[O:14])[CH2:11][CH3:12].[C:17]1([S:23]([N:26]2[C:30]3=[N:31][CH:32]=[C:33]([NH:42][C:43](=[O:47])[CH2:44][C:45]#[N:46])[C:34]([NH:35][CH:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)=[C:29]3[CH:28]=[CH:27]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[C:17]1([S:23]([N:26]2[C:30]3=[N:31][CH:32]=[C:33]([NH:42][C:43](=[O:47])[CH2:44][C:45]#[N:46])[C:34]([NH:35][CH:36]4[CH2:41][CH2:40][N:39]([S:13]([CH2:10][CH2:11][CH3:12])(=[O:15])=[O:14])[CH2:38][CH2:37]4)=[C:29]3[CH:28]=[CH:27]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 662791-Propanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67379316N-[1-benzenesulfonyl-4-(piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyano-acetamide

Produkt 1

HCID 67342235N-{1-benzenesulfonyl-4-[1-(propane-1-sulfonyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-2-cyano-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Diisopropylethylamine (0.107 ml, 0.615 mmol) and 1-propanesulfonyl chloride (0.035 ml, 0.308 mmol) were added sequentially to a solution of N-[1-benzenesulfonyl-4-(piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyano-acetamide (hydrochloride salt) (0.205 mmol) in CH2Cl2 (2 ml) at 25° C. The reaction mixture was stirred for 3 h at 25° C., then was partitioned between saturated NaHCO3 (6 ml) and CH2Cl2 (2 ml). The phases were separated using a phase separation column (Biotage) and the organic layer was concentrated under reduced pressure to give crude N-{1-benzenesulfonyl-4-[1-(propane-1-sulfonyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-2-cyano-acetamide as a brown oil/solid. LCMS (Method G, ESI): RT=0.88 min, m+H=545.3. This material was used in the next step below without additional purification or characterization.

Aufarbeitung

  1. customwas partitioned between saturated NaHCO3 (6 ml) and CH2Cl2 (2 ml)
  2. customThe phases were separated
  3. customa phase separation column (Biotage)
  4. concentrationthe organic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f8f9860aafb34080842809f1d60ab7d0
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461328B2

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