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

HRID 1257595Notes

Reaction equation

Cl.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[C:21]([NH:22][C:23](=[O:30])[CH2:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:20][N:19]=[C:18]3[N:31]([S:34]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)(=[O:36])=[O:35])[CH:32]=[CH:33][C:17]=23)[CH2:11][CH2:10]1)=O)(C)(C)C>O1CCOCC1>[C:37]1([S:34]([N:31]2[C:18]3=[N:19][CH:20]=[C:21]([NH:22][C:23](=[O:30])[CH2:24][CH:25]4[CH2:26][CH2:27][CH2:28][CH2:29]4)[C:16]([NH:15][CH:12]4[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]4)=[C:17]3[CH:33]=[CH:32]2)(=[O:36])=[O:35])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A 4.0 M solution of HCl in 1,4-dioxane (10 ml) was added to a solution of 4-[1-benzenesulfonyl-5-(2-cyclopentyl-acetylamino)-1H-pyrrolo[2,3-b]pyridin-4-ylamino]-piperidine-1-carboxylic acid tert-butyl ester (0.222 g, 0.382 mmol) in 1,4-dioxane (10 ml) at 25° C. The reaction mixture was stirred at 25° C. for 1 h, then was concentrated under reduced pressure to afford crude N-[1-benzenesulfonyl-4-(piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyclopentyl-acetamide (hydrochloride salt) as a white solid. This material was used in the next step below without additional purification or characterization.

Workup

concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-6615664e829d40cabe923878150e6399
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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