Ethanol hydrochloride → (2Z)-3-(5-chloro-6-{[(3R)-1-cyclopentyl-3-pyrrolidinyl]amino}-3-pyridinyl)-2-fluoro-N-hydroxyacrylamide dihydrochloride

HRID 2376194Notes

Reaction equation

[ClH:1].CCO.[Cl:5][C:6]1[CH:7]=[C:8](/[CH:23]=[C:24](\[F:35])/[C:25]([NH:27][O:28]C2CCCCO2)=[O:26])[CH:9]=[N:10][C:11]=1[NH:12][C@@H:13]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:14]1>CCO>[ClH:5].[ClH:1].[Cl:5][C:6]1[CH:7]=[C:8](/[CH:23]=[C:24](\[F:35])/[C:25]([NH:27][OH:28])=[O:26])[CH:9]=[N:10][C:11]=1[NH:12][C@@H:13]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[CH2:14]1

Participants

Conditions

Temperature: 22.5 °C

Procedure

A solution of 2N HCl-EtOH solution (3.4 ml) was added to a mixture of (2Z)-3-(5-chloro-6-{[(3R)-1-cyclopentyl-3-pyrrolidinyl]amino}-3-pyridinyl)-2-fluoro-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (620 mg) in EtOH (5 ml) and stirred at 20-25° C. for 2 hours. IPE (20 ml) was added to a reaction mixture and the resultant mixture was stirred at ambient temperature for 20 minutes. The precipitate was collected by filtration to give (2Z)-3-(5-chloro-6-{[(3R)-1-cyclopentyl-3-pyrrolidinyl]amino}-3-pyridinyl)-2-fluoro-N-hydroxyacrylamide dihydrochloride (500 mg).

Workup

additionIPE (20 ml) was added to a reaction mixture
filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-97f9c17255c340d2906be9bd0b4f48e5
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465731B2

Reaction notes

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