Hydrochloric Acid → 4-{5-[4-(piperazine-1-carbonyl)-phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-benzamide, hydrochloride salt

HRID 85053Notes

Reaction equation

HRID 85053 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:39])[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[C:23]4[C:29]([C:30]5[CH:35]=[CH:34][C:33]([C:36](=[O:38])[NH2:37])=[CH:32][CH:31]=5)=[CH:28][NH:27][C:24]4=[N:25][CH:26]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:40]>CO.O1CCOCC1>[ClH:40].[N:11]1([C:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[C:23]4[C:29]([C:30]5[CH:31]=[CH:32][C:33]([C:36]([NH2:37])=[O:38])=[CH:34][CH:35]=5)=[CH:28][NH:27][C:24]4=[N:25][CH:26]=3)=[CH:17][CH:16]=2)=[O:39])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 667796424-{4-[3-(4-carbamoyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 1317319134-{5-[4-(piperazine-1-carbonyl)-phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-benzamide, hydrochloride saltYield 116%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-{4-[3-(4-carbamoyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester (100 mg, 0.19 mmol) in MeOH (3 ml) was treated with 4 N HCl in dioxane (2.5 ml) and stirred at room temperature for 1 hr. The mixture was evaporated, taken up in MeOH and evaporated again. This was repeated twice to give 102 mg (116%) of the title compound. MS ESI (m/z): MS ESI (m/z): 426.4 (M+1)+, calc. 425.

Workup

  1. customThe mixture was evaporated
  2. customevaporated again

Sources & evidence

ORD record
ord-7bc33a4c827248d0aa9dfe9ab5554991
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

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