Hydrochloric Acid → (E)-3-(2-{3-[(Aminocarbonyl)oxy]piperidino}-8-{[(4-cyclobutyl-1,3-thiazol-2-yl)-amino]carbonyl}-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-2-propenoic acid

HRID 1828461Notes

Reaction equation

HRID 1828461 reaction equation
[NH2:1][C:2]([O:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:12]=[C:13]3[CH:30]=[C:29]([C:31]([NH:33][C:34]4[S:35][CH:36]=[C:37]([CH:39]5[CH2:42][CH2:41][CH2:40]5)[N:38]=4)=[O:32])[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:3].Cl>O1CCOCC1>[NH2:1][C:2]([O:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:12]=[C:13]3[CH:30]=[C:29]([C:31]([NH:33][C:34]4[S:35][CH:36]=[C:37]([CH:39]5[CH2:42][CH2:41][CH2:40]5)[N:38]=4)=[O:32])[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:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86588106tert-Butyl (E)-3-(2-{3-[(aminocarbonyl)oxy]piperidino}-8-{[(4-cyclobutyl-1,3-thiazol-2-yl)amino]carbonyl}-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-2-propenoate

Product 1

HCID 22063626(E)-3-(2-{3-[(Aminocarbonyl)oxy]piperidino}-8-{[(4-cyclobutyl-1,3-thiazol-2-yl)-amino]carbonyl}-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-2-propenoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (E)-3-(2-{3-[(aminocarbonyl)oxy]piperidino}-8-{[(4-cyclobutyl-1,3-thiazol-2-yl)amino]carbonyl}-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-2-propenoate (20 mg, 0.034 mmol) was added with a mixed solution of 4 N hydrochloric acid and dioxane (1.5 ml) at room temperature and stirred for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=10:1) to obtain 9 mg (58% for the two steps) of the title compound as yellow crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-e9d6e38a90e841168e9c7d6be00beff0
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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