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Hydrochloride methanol → (2E)-3-{6-[(1-benzyl-3-pyrrolidinyl)amino]-3-pyridyl}-N-hydroxyacrylamide dihydrochloride

HRID 226466
Notes
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Reaction equation

HRID 226466 reaction equation
[ClH:1].CO.[CH2:4]([N:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]2[N:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([NH:27][O:28]C3CCCCO3)=[O:26])=[CH:19][CH:18]=2)[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO>[ClH:1].[ClH:1].[CH2:4]([N:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]2[N:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([NH:27][OH:28])=[O:26])=[CH:19][CH:18]=2)[CH2:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 86603614(2E)-3-{6-[(1-benzyl-3-pyrrolidinyl)amino]-3-pyridyl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide

Product 1

HCID 86603770(2E)-3-{6-[(1-benzyl-3-pyrrolidinyl)amino]-3-pyridyl}-N-hydroxyacrylamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 10% HCl-MeOH solution (0.75 ml) was added to a mixture of (2E)-3-{6-[(1-benzyl-3-pyrrolidinyl)amino]-3-pyridyl}-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (170 mg) in MeOH 3 ml) and stirred at 15-25° C. for 2 hours. The reaction mixture was evaporated in vacuo and the residue was triturated with small amount MeOH and acetone and the precipitate was collected by filtration to give (2E)-3-{6-[(1-benzyl-3-pyrrolidinyl)amino]-3-pyridyl}-N-hydroxyacrylamide dihydrochloride (107 mg)

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was triturated with small amount MeOH and acetone
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-47e64e536fa04d1e9c67e5fabb11521d
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07557127B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes