Methanesulfonyl chloride → N-[1-benzenesulfonyl-4-(1-methanesulfonyl-piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyclopentyl-acetamide

HRID 1257596Notes

Reaction equation

HRID 1257596 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][S:11](Cl)(=[O:13])=[O:12].[C:15]1([S:21]([N:24]2[C:28]3=[N:29][CH:30]=[C:31]([NH:40][C:41](=[O:48])[CH2:42][CH:43]4[CH2:47][CH2:46][CH2:45][CH2:44]4)[C:32]([NH:33][CH:34]4[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]4)=[C:27]3[CH:26]=[CH:25]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[C:15]1([S:21]([N:24]2[C:28]3=[N:29][CH:30]=[C:31]([NH:40][C:41](=[O:48])[CH2:42][CH:43]4[CH2:44][CH2:45][CH2:46][CH2:47]4)[C:32]([NH:33][CH:34]4[CH2:35][CH2:36][N:37]([S:11]([CH3:10])(=[O:13])=[O:12])[CH2:38][CH2:39]4)=[C:27]3[CH:26]=[CH:25]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67379631N-[1-benzenesulfonyl-4-(piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyclopentyl-acetamide

Product 1

HCID 67346024N-[1-benzenesulfonyl-4-(1-methanesulfonyl-piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyclopentyl-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Diisopropylethylamine (0.166 ml, 0.954 mmol) and methanesulfonyl chloride (0.027 ml, 0.350 mmol), were added sequentially to a solution of crude N-[1-benzenesulfonyl-4-(piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyclopentyl-acetamide (hydrochloride salt) (0.382 mmol, obtained in preceding step) in CH2Cl2 (10 ml) at 25° C. The reaction mixture was stirred for 30 min at 25° C., then was partitioned between half-saturated NaHCO3 (75 ml) and CH2Cl2 (100 ml). The organic layer was dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure to afford N-[1-benzenesulfonyl-4-(1-methanesulfonyl-piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyclopentyl-acetamide as a white foam. LCMS (Method G, ESI): RT=0.93 min, m+H=560.3. This material was used in the next step below without additional purification or characterization.

Workup

  1. customwas partitioned between half-saturated NaHCO3 (75 ml) and CH2Cl2 (100 ml)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-545b15805a834b14b3c546aae4eaa812
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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