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

HRID 1828500Notes

Reaction equation

HRID 1828500 reaction equation
[CH3:1][N:2]([CH3:41])[C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:12]=[C:13]3[CH:30]=[C:29](/[CH:31]=[CH:32]/[C:33]4[S:34][CH:35]=[C:36]([CH:38]([CH3:40])[CH3:39])[N:37]=4)[CH:28]=[CH:27][N:14]3[C:15](=[O:26])[C:16]=2/[CH:17]=[CH:18]/[C:19]([O:21]C(C)(C)C)=[O:20])[CH2:6]1)=[O:4].FC(F)(F)C(O)=O>>[CH3:41][N:2]([CH3:1])[C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:12]=[C:13]3[CH:30]=[C:29](/[CH:31]=[CH:32]/[C:33]4[S:34][CH:35]=[C:36]([CH:38]([CH3:39])[CH3:40])[N:37]=4)[CH:28]=[CH:27][N:14]3[C:15](=[O:26])[C:16]=2/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])[CH2:6]1)=[O:4]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86588133tert-butyl (E)-3-(2-{3-[(dimethylamino)carbonyl]piperidino}-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-2-propenoate2×

Product 1

HCID 86588132(E)-3-(2-(3-[(Dimethylamino)carbonyl]piperidino}-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-2-propenoic acidYield 61%

Procedure

The tert-butyl (E)-3-(2-{3-[(dimethylamino)carbonyl]piperidino}-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-2-propenoate (71.0 mg, 0.123 mmol) obtained in (B) was added with trifluoroacetic acid (3.0 ml) and stirred at room temperature for 2 hours. The trifluoroacetic acid in the reaction mixture 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 (39.0 mg, 61%).

Workup

  1. customThe trifluoroacetic acid in the reaction mixture 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-90561f25c9894899b8fc24cca59631c8
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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