Trifluoroacetic acid → (E)-3-(8-[(E)-2-(4-Isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-2-(3-[(methylamino)-carbonyl]piperidino}-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-2-propenoic acid

HRID 1828502Notes

Reaction equation

HRID 1828502 reaction equation
[CH:1]([C:4]1[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]2[CH:40]=[CH:39][N:14]3[C:15](=[O:38])[C:16](/[CH:29]=[CH:30]/[C:31]([O:33]C(C)(C)C)=[O:32])=[C:17]([N:19]4[CH2:24][CH2:23][CH2:22][CH:21]([C:25]([NH:27][CH3:28])=[O:26])[CH2:20]4)[N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].FC(F)(F)C(O)=O>>[CH:1]([C:4]1[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]2[CH:40]=[CH:39][N:14]3[C:15](=[O:38])[C:16](/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32])=[C:17]([N:19]4[CH2:24][CH2:23][CH2:22][CH:21]([C:25]([NH:27][CH3:28])=[O:26])[CH2:20]4)[N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86588136tert-Butyl (E)-3-(8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-2-{3-[(methylamino)carbonyl]piperidino}-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate2×

Product 1

HCID 86588135(E)-3-(8-[(E)-2-(4-Isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-2-(3-[(methylamino)-carbonyl]piperidino}-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-2-propenoic acidYield 28.3%

Procedure

The tert-butyl (E)-3-(8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-2-{3-[(methylamino)carbonyl]piperidino}-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-2-propenoate (192 mg, 0.341 mmol) obtained in (B) was added with trifluoroacetic acid (5.0 ml) and stirred at room temperature for 1.5 hours. After the reaction was completed, the trifluoroacetic acid was evaporated under reduced pressure, and the residue was neutralized with 0.1 N sodium hydroxide and phosphate buffer (pH 7-8) and extracted with chloroform. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by thin layer chromatography (chloroform:methanol and chloroform:methanol:water=8:3:1, v/v, lower layer) to obtain the title compound (49.0 mg, 28%).

Workup

  1. customthe trifluoroacetic acid was evaporated under reduced pressure
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by thin layer chromatography (chloroform:methanol and chloroform:methanol:water=8:3:1, v/v, lower layer)

Sources & evidence

ORD record
ord-09cc934d074e498590e94c2ed5881a0c
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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