Hydrochloric Acid → (E)-3-{2-(3-Hydroxypiperidino)-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 1828490Notes

Reaction equation

HRID 1828490 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:9]=[C:10]3[CH:27]=[C:26](/[CH:28]=[CH:29]/[C:30]4[S:31][CH:32]=[C:33]([CH:35]([CH3:37])[CH3:36])[N:34]=4)[CH:25]=[CH:24][N:11]3[C:12](=[O:23])[C:13]=2/[CH:14]=[CH:15]/[C:16]([O:18]C(C)(C)C)=[O:17])[CH2:3]1.Cl>O1CCOCC1>[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:9]=[C:10]3[CH:27]=[C:26](/[CH:28]=[CH:29]/[C:30]4[S:31][CH:32]=[C:33]([CH:35]([CH3:37])[CH3:36])[N:34]=4)[CH:25]=[CH:24][N:11]3[C:12](=[O:23])[C:13]=2/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])[CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86588119tert-Butyl (E)-3-{2-(3-hydroxypiperidino)-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 86588121(E)-3-{2-(3-Hydroxypiperidino)-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 49%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The tert-Butyl (E)-3-{2-(3-hydroxypiperidino)-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate (43.4 mg, 0.0830 mmol) obtained in (H) was dissolved in 1,4-dioxane (200 μl), added with 4 N hydrochloric acid solution in 1,4-dioxane, and stirred at room temperature for 3.5 hours. The reaction solution was concentrated, and the residue was purified by thin layer chromatography (chloroform:methanol:water=10:1:0→8:3:0.1→7:3:1, v/v) to obtain the title compound (18.9 mg, 49%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified by thin layer chromatography (chloroform

Sources & evidence

ORD record
ord-f4d897b1a53241e3a2d49c9e47a8d4a2
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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