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

HRID 885883Notes

Reaction equation

C([O:5][C:6](=[O:17])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][N:10]=1)(C)(C)C.[OH-].[K+].[CH3:20][C@H:21]1[N:26]([CH3:27])[C@@H:25]([CH3:28])[CH2:24][N:23]([C:29]2[CH:30]=[C:31]([C:35](=[O:37])[CH3:36])[CH:32]=[CH:33][CH:34]=2)[CH2:22]1>CCO>[O:37]=[C:35]([C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([N:23]2[CH2:22][C@H:21]([CH3:20])[N:26]([CH3:27])[C@H:25]([CH3:28])[CH2:24]2)[CH:30]=1)/[CH:36]=[CH:15]/[C:12]1[CH:13]=[CH:14][C:9](/[CH:8]=[CH:7]/[C:6]([OH:5])=[O:17])=[N:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of (E)-3-(5-formyl-pyridin-2-yl)-acrylic acid tert-butyl ester (described in Example 11 STEP A-D, 168 mg, 0.718 mmol), 1.7 M KOH (0.674 ml) and 1-[3-((3R,5S)-3,4,5-trimethyl-piperazin-1-yl)-phenyl]-ethanone (described in Preparation 8, 188 mg, 0.764 mmol) in EtOH (7 ml) was stirred at 0° C. for 6 h. The resulting precipitate was filtered off and dissolved in DCM (5 ml) and TFA (1 ml). The mixture was stirred at room temperature for 4 h and then the solvent was removed in vacuo to give 282 mg of (E)-3-(5-{(E)-3-oxo-3-[3-((3R,5S)-3,4,5-trimethyl-piperazin-1-yl)-phenyl]-propenyl}-pyridin-2-yl)-acrylic acid as its bis-trifluoroacetate salt.

Workup

filtrationThe resulting precipitate was filtered off
dissolutiondissolved in DCM (5 ml)
stirringThe mixture was stirred at room temperature for 4 h
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-a91dfc44a5d541eea059a9b9c702689c
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242175B2

Reaction notes

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