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

HRID 1257599Notes

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

Participants

Conditions

Temperature: 25 °C

Procedure

A 4.0 M solution of HCl in 1,4-dioxane (4 ml) was added to a solution of 4-[1-benzenesulfonyl-5-(2-cyano-acetylamino)-1H-pyrrolo[2,3-b]pyridin-4-ylamino]-piperidine-1-carboxylic acid tert-butyl ester (1.44 mmol) in 1,4-dioxane (2 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-cyano-acetamide (hydrochloride salt) as a brown 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-3a7e5d078e8a42a5aebeda5bda209aa1
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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