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

HRID 2376165Notes

Reaction equation

HRID 2376165 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

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

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% 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-4a195f16f66540a0b763c62ac2f6d0a6
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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