Hydrochloric Acid → (2E)-3-[5-({(3R)-1-[2-(dimethylamino) benzyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]-N-hydroxyacrylamide trihydrochloride

HRID 2354103Notes

Reaction equation

HRID 2354103 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]1[CH:33]=[CH:32][CH:31]=[CH:30][C:4]=1[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:12]2[N:13]=[CH:14][C:15](/[CH:18]=[CH:19]/[C:20]([NH:22][O:23]C3CCCCO3)=[O:21])=[N:16][CH:17]=2)[CH2:7]1.[ClH:35]>CO.CCO>[ClH:35].[ClH:35].[ClH:35].[CH3:34][N:2]([CH3:1])[C:3]1[CH:33]=[CH:32][CH:31]=[CH:30][C:4]=1[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:12]2[N:13]=[CH:14][C:15](/[CH:18]=[CH:19]/[C:20]([NH:22][OH:23])=[O:21])=[N:16][CH:17]=2)[CH2:7]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86628129(2E)-3-[5-({(3R)-1-[2-(dimethylamino)benzyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide

Product 1

HCID 136381712(2E)-3-[5-({(3R)-1-[2-(dimethylamino) benzyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]-N-hydroxyacrylamide trihydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of (2E)-3-[5-({(3R)-1-[2-(dimethylamino)benzyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (236 mg) in MeOH (3.5 mL) was added 2N—HCl solution in EtOH (1.27 mL), which was stirred at room temperature for 1 hour. To the reaction mixture was dropwised IPE (9.4 mL), which was stirred further more 1 hour. The prepicitate was filtered to give (2E)-3-[5-({(3R)-1-[2-(dimethylamino) benzyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]-N-hydroxyacrylamide trihydrochloride as a yellow powder (241 mg).

Workup

  1. stirringwas stirred further more 1 hour
  2. filtrationThe prepicitate was filtered

Sources & evidence

ORD record
ord-d212853be49347c2bccaf324f8e5ff51
Source dataset
uspto-grants-2010_07
Patent number
US07750155B2

Reaction notes

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