Hydrochloric Acid → (E)-3-{2-(3-Hydroxypiperidino)-8-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoic acid

HRID 1828433Notes

Reaction equation

HRID 1828433 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]([O:28][CH2:29][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]([O:28][CH2:29][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 86588098tert-Butyl (E)-3-{2-(3-hydroxypiperidino)-8-[(4-isopropyl-1,3-thiazol-2-yl)-methoxy]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate

Product 1

HCID 22063778(E)-3-{2-(3-Hydroxypiperidino)-8-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoic acidYield 110.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (E)-3-{2-(3-hydroxypiperidino)-8-[(4-isopropyl-1,3-thiazol-2-yl)-methoxy]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate (24 mg, 0.046 mmol) was added with a mixture of 4 N hydrochloric acid and dioxane (1 ml) and stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by thin layer silica gel chromatography (chloroform:methanol=15:1) to obtain 24 mg (100%) of the title compound as yellow crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by thin layer silica gel chromatography (chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-482e5175ae514b90bb0210704ce3a83f
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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