Hydrochloric Acid → HCID 67344293, compound

HRID 1257735Notes

Reaction equation

HRID 1257735 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]3[N:25]([S:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)(=[O:30])=[O:29])[CH:26]=[CH:27][C:17]=23)[CH2:10]1)=O)(C)(C)C>O1CCOCC1>[ClH:1].[C:31]1([S:28]([N:25]2[C:18]3=[N:19][CH:20]=[C:21]([N+:22]([O-:24])=[O:23])[C:16]([NH:15][CH:11]4[CH2:12][CH2:13][CH2:14][NH:9][CH2:10]4)=[C:17]3[CH:27]=[CH:26]2)(=[O:29])=[O:30])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67345319HCID 67345319, compound

Product 1

HCID 67344293HCID 67344293, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

A 4.0 M solution of HCl in 1,4-dioxane (60 ml) was added to 3-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (6.11 g, 12.2 mmol) dissolved in 1,4-dioxane (30 ml) at 25° C. The resulting suspension mixture was stirred at 50° C. for 2 h, then was cooled to 25° C. and was concentrated under reduced pressure. Toluene (80 ml) was added to the residue and the mixture was again concentrated under reduced pressure to give crude (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-piperidin-3-yl-amine hydrochloride as a yellow solid. This material was used in the next step below without additional characterization or purification.

Workup

  1. temperaturewas cooled to 25° C.
  2. concentrationwas concentrated under reduced pressure
  3. additionToluene (80 ml) was added to the residue
  4. concentrationthe mixture was again concentrated under reduced pressure

Sources & evidence

ORD record
ord-163e0588eec348cd9f82581c365b9fd9
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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