Propionic Acid → N-{1-benzenesulfonyl-4-[1-(2-cyano-1-methyl-ethyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-propionamide

HRID 1257615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257615
[C:1]([OH:5])(=O)[CH2:2][CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:39][C:40]1[C:41]([NH:58][CH:59]2[CH2:64][CH2:63][N:62]([CH:65]([CH3:69])[CH2:66][C:67]#[N:68])[CH2:61][CH2:60]2)=[C:42]2[CH:48]=[CH:47][N:46]([S:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)(=[O:51])=[O:50])[C:43]2=[N:44][CH:45]=1>CN(C=O)C.C(Cl)Cl>[C:52]1([S:49]([N:46]2[C:43]3=[N:44][CH:45]=[C:40]([NH:39][C:1](=[O:5])[CH2:2][CH3:3])[C:41]([NH:58][CH:59]4[CH2:60][CH2:61][N:62]([CH:65]([CH3:69])[CH2:66][C:67]#[N:68])[CH2:63][CH2:64]4)=[C:42]3[CH:48]=[CH:47]2)(=[O:50])=[O:51])[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Komponenten

7

Edukt 4

HCID 1032Propionic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673436313-[4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidin-1-yl]-butyronitrile

Produkt 1

HCID 67343906N-{1-benzenesulfonyl-4-[1-(2-cyano-1-methyl-ethyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Propionic acid (0.0176 ml, 0.320 mmol), HATU (0.122 g, 0.320 mmol), and diisopropylethylamine (0.062 ml, 0.358 mmol) were added sequentially to a solution of 3-[4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidin-1-yl]-butyronitrile (0.134 g, 0.305 mmol) in a 4:1 mixture of CH2Cl2 and DMF (5 ml) at 25° C. The reaction mixture was stirred for 14 h at 25° C., then was partitioned between saturated NaHCO3 (4 ml) and CH2Cl2 (3 ml). The phases were separated using a phase separator column (Biotage) and the organic layer was concentrated under reduced pressure to afford crude N-{1-benzenesulfonyl-4-[1-(2-cyano-1-methyl-ethyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-propionamide as a brown oil. LCMS (Method G, ESI): RT=0.60 min, m+H=495.3. This material was used in the next step below without additional purification or characterization.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7da0bb9abd63467bbd0ab73a9ec81faf
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461328B2

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