Potassium Hydroxide → (E)-3-(5-{(E)-3-[4-(4-benzyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-pyridin-2-yl)-acrylic acid

HRID 885881Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:27][C:28](=[O:39])/[CH:29]=[CH:30]/[C:31]1[CH:36]=[CH:35][C:34]([CH:37]=O)=[CH:33][N:32]=1)(C)(C)C.[OH-].[K+]>CCO>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20](=[O:22])/[CH:21]=[CH:37]/[C:34]3[CH:35]=[CH:36][C:31](/[CH:30]=[CH:29]/[C:28]([OH:39])=[O:27])=[N:32][CH:33]=3)=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 1-[4-(4-benzyl-piperazin-1-yl)-phenyl]-ethanone (319 mg, 1.085 mmol), (E)-3-(5-formyl-pyridin-2-yl)-acrylic acid tert-butyl ester (described in Example 11 STEP A-D, 253 mg, 1.08 mmol) and KOH 1.7 M (0.638 ml) in EtOH (10 ml) was stirred at 0° C. overnight. The resulting precipitate was filtered washing with hot EtOH and the powder was dissolved in DCM (10 ml) and treated with TFA (2 ml) for 6 h. The solvent was then removed in vacuo to give 388 mg of (E)-3-(5-{(E)-3-[4-(4-benzyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-pyridin-2-yl)-acrylic acid as its bis-trifluoroacetate salt.

Workup

filtrationThe resulting precipitate was filtered
washwashing with hot EtOH
dissolutionthe powder was dissolved in DCM (10 ml)
additiontreated with TFA (2 ml) for 6 h
customThe solvent was then removed in vacuo

Sources & evidence

ORD record: ord-638258a9c21c4a719271176b4792a36f
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242175B2

Reaction notes

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