Hydrochloric Acid → (E)-N-[2-[(2-acetyl-4-pyridyl)amino]ethyl]-4,4,5,5,5-pentafluoro-pent-2-enamide

HRID 333064Notes

Reaction equation

[F:1][C:2]([F:27])([C:23]([F:26])([F:25])[F:24])/[CH:3]=[CH:4]/[C:5]([NH:7][CH2:8][CH2:9][NH:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]2([CH3:22])OCC[O:18]2)[CH:12]=1)=[O:6].Cl>CC(C)=O.O>[C:17]([C:13]1[CH:12]=[C:11]([NH:10][CH2:9][CH2:8][NH:7][C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:1])([F:27])[C:23]([F:26])([F:24])[F:25])[CH:16]=[CH:15][N:14]=1)(=[O:18])[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

(E)-4,4,5,5,5-Pentafluoro-N-[2-[[2-(2-methyl-1,3-dioxolan-2-yl)-4-pyridyl]amino]ethyl]pent-2-enamide (35 mg, 0.09 mmol) was dissolved in aceton (1 ml), 4M hydrochloric acid (0.5 ml) was added and the mixture was stirred in a closed vessel at 100° C. for 15 minutes with microwave heating. The mixture was diluted with water, extracted with ethyl acetate and the organic phase was washed with brine, dried over magnesium sulfate and evaporated to dryness. The resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 2.5 mg (0.0071 mmol, 7.9%).

Workup

extractionextracted with ethyl acetate
washthe organic phase was washed with brine
dry with materialdried over magnesium sulfate
customevaporated to dryness
customThe resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
customto yield 2.5 mg (0.0071 mmol, 7.9%)

Sources & evidence

ORD record: ord-e4c6eb12c2b64977ad65a8c908d34c59
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877934B2

Reaction notes

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