Hydrochloric Acid → HCID 59278515, compound

HRID 1698240Notes

Reaction equation

HRID 1698240 reaction equation
CC(S([NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]([NH2:19])=[O:18])[CH:12]=1)[CH2:9][CH3:10])=O)(C)C.Cl>CO.O1CCOCC1>[NH2:7][C@H:8]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]([NH2:19])=[O:18])[CH:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 59278114HCID 59278114, compound

Product 1

HCID 59278515HCID 59278515, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 85% 4-[(S)-1-(2-methyl-propane-2-sulfinylamino)-propyl]-pyridine-2-carboxylic acid amide (5.5 g, 16.5 mmol) in methanol (50 mL) was added a 4 N solution of HCl in dioxane (4.33 mL, 17.32 mmol). After 2 hour, additional 4 N HCl in dioxane (0.5 mL) was added. The reaction was monitored by TLC (eluting with EtOAc). After 1.5 hours, the mixture was concentrated in vacuo to remove MeOH and EtOAc (400 mL) was added. The mixture was washed with saturated sodium carbonate solution (100 mL) and the aqueous layer was extracted with EtOAc (4×100 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to afford 4-((S)-1-amino-propyl)-pyridine-2-carboxylic acid amide.

Workup

  1. washThe reaction was monitored by TLC (eluting with EtOAc)
  2. waitAfter 1.5 hours
  3. concentrationthe mixture was concentrated in vacuo
  4. customto remove MeOH and EtOAc (400 mL)
  5. additionwas added
  6. washThe mixture was washed with saturated sodium carbonate solution (100 mL)
  7. extractionthe aqueous layer was extracted with EtOAc (4×100 mL)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-09126f602ce0461b8e4aa41cec8953c4
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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