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

HRID 1257608Notes

Reaction equation

HRID 1257608 reaction equation
[C:1]([OH:6])(=O)[CH2:2][CH2:3][CH3:4].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:40][C:41]1[C:42]([NH:59][CH:60]2[CH2:65][CH2:64][N:63]([CH2:66][CH2:67][C:68]#[N:69])[CH2:62][CH2:61]2)=[C:43]2[CH:49]=[CH:48][N:47]([S:50]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)(=[O:52])=[O:51])[C:44]2=[N:45][CH:46]=1>CN(C=O)C.C(Cl)Cl>[C:53]1([S:50]([N:47]2[C:44]3=[N:45][CH:46]=[C:41]([NH:40][C:1](=[O:6])[CH2:2][CH2:3][CH3:4])[C:42]([NH:59][CH:60]4[CH2:61][CH2:62][N:63]([CH2:66][CH2:67][C:68]#[N:69])[CH2:64][CH2:65]4)=[C:43]3[CH:49]=[CH:48]2)(=[O:51])=[O:52])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

7

Reactant 4

HCID 264Butyric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673456183-[4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidin-1-yl]-propionitrile

Product 1

HCID 67348422N-{1-benzenesulfonyl-4-[1-(2-cyano-ethyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-butyramide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Butyric acid (0.029 ml, 0.321 mmol), diisopropylethylamine (0.065 ml, 0.375 mmol), and HATU (0.122 g, 0.321 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]-propionitrile (0.130 g, 0.306 mmol, prepared as described in Example 118) in a 4:1 mixture of CH2Cl2 and DMF (5 ml) at 25° C. The reaction mixture was stirred for 15 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-(2-cyano-ethyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-butyramide as a brown oil. LCMS (Method G, ESI): RT=0.59 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 (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

Sources & evidence

ORD record
ord-2401f59963674ec0b606610729d6b5c1
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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