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 1257615Notes

Reaction equation

HRID 1257615 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7da0bb9abd63467bbd0ab73a9ec81faf
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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