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

HRID 226466Notes

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

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

customThe reaction mixture was evaporated in vacuo
customthe residue was triturated with small amount MeOH and acetone
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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