Hydrochloric Acid → HCID 68955704, compound

HRID 1971293Notes

Reaction equation

HRID 1971293 reaction equation
[CH2:1]([N:3]([CH3:17])[C:4]([CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[O:9]C=[N:7]1)=[O:5])[CH3:2].C(N(C)C([C@H]1[C@H](C2C=CN=CC=2)OC=N1)=O)C.Cl>CO>[NH2:7][CH:6]([CH:10]([OH:9])[C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1)[C:4]([N:3]([CH2:1][CH3:2])[CH3:17])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68959930HCID 68959930, compoundHCID 68962583HCID 68962583, compound

Product 1

HCID 68955704HCID 68955704, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-ethyl-4,5-dihydro-N-methyl-5-(pyridin-4-yl)oxazole-4-carboxamide SLA 09190 (144 mg, 0.6 mmol) in MeOH (5 mL) was added a solution of HCl 37% (240 μL). The reaction was stirred for 3 h at 50° C. and concentrated under reduced pressure. The resulting product was dissolved in MeOH and treated with amberlite (OH− form), filtered to give after evaporation a residue that was purified by column chromatography (SiO2, with a gradient of MeOH 10% in CH2Cl2) to yield to 2-amino-N-ethyl-3-hydroxy-N-methyl-3-pyridin-4-yl-propionamide. The hydrochloride salt was formed by treatment of this free base with a solution of HCl 1 M in MeOH (1 mL) to give after evaporation 2-amino-N-ethyl-3-hydroxy-N-methyl-3-pyridin-4-yl-propanamide dihydrochloride Compound 250 as a pale yellow solid (80 mg, 44% yield).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resulting product was dissolved in MeOH
  3. additiontreated with amberlite (OH− form)
  4. filtrationfiltered
  5. customto give
  6. customafter evaporation a residue that
  7. customwas purified by column chromatography (SiO2

Sources & evidence

ORD record
ord-2253415bdc2547e08fd76af4429bf863
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

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