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Hydrochloric Acid → 1-[1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]piperazin-2-one, hydrochloride

HRID 1622884
Notes
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Reaction equation

HRID 1622884 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:9][CH:10]=[C:5]2[C:4]([N:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][C:20]2=[O:32])=[CH:3]1.[ClH:33]>C(Cl)Cl.CCOC(C)=O>[ClH:33].[CH3:1][N:2]1[C:6]2=[N:7][C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:9][CH:10]=[C:5]2[C:4]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][C:20]2=[O:32])=[CH:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67817033tert-butyl 4-[1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxopiperazine-1-carboxylate

Product 1

HCID 1317316621-[1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]piperazin-2-one, hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

To a solution of tert-butyl 4-[1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxopiperazine-1-carboxylate (0.278 g, 0.653 mmol) in DCM (10 mL) is added a saturated solution of hydrogen chloride in EtOAc (6 mL) at room temperature, and the reaction mixture stirred at room temperature for 67 h. The solvent is carefully decanted off and the residue triturated with Et2O/MeOH. The solvent is again decanted off and the residue further triturated with Et2O/MeOH. The resultant residue is dried in vacuo for 3 h. to give the title compound (0.217 g, 0.580 mmol) as a pale yellow solid. MS (m/z): 338 (M+1).

Workup

  1. customThe solvent is carefully decanted off
  2. customthe residue triturated with Et2O/MeOH
  3. customThe solvent is again decanted off
  4. customthe residue further triturated with Et2O/MeOH
  5. dry with materialThe resultant residue is dried in vacuo for 3 h.

Sources & evidence

ORD record
ord-24de85ccbf9c48b098e959a03988997d
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778946B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes