Hydrochloric Acid → HCID 54591670, compound

HRID 509256Notes

Reaction equation

HRID 509256 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1[N:19]=[C:18]([N:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][C:28]([O:30]C)=[O:29])[CH2:22][CH2:21]3)[CH:17]=[CH:16][CH:15]=1)=[O:13])[CH2:8]2.Cl>CO>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1[N:19]=[C:18]([N:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH2:22][CH2:21]3)[CH:17]=[CH:16][CH:15]=1)=[O:13])[CH2:8]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54591669HCID 54591669, compound

Product 1

HCID 54591670HCID 54591670, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(4-(6-(adamantan-2-ylcarbamoyl)pyridin-2-yl)piperazin-1-yl)propanoate (43 mg, 0.101 mmol) was added into 4N aqueous HCl solution (2 ml), and heated at reflux for 2 hours. The resulting reaction liquid was concentrated under reduced pressure, and then neutralized by slow addition of a saturated aqueous NaHCO3 solution, followed by extraction with a mixture solution (10 ml×2) of THF:MC=4:1. The organic layer was dried over anhydrous magnesium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (10% MeOH/MC), to obtain 27 mg of pale yellow oil (65%). MS (ESI): 413 [M+H]+

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThe resulting reaction liquid
  4. concentrationwas concentrated under reduced pressure
  5. additionneutralized by slow addition of a saturated aqueous NaHCO3 solution
  6. extractionfollowed by extraction with a mixture solution (10 ml×2) of THF
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfollowed by filtration and concentration
  9. customthe residue thus obtained

Sources & evidence

ORD record
ord-7092de13dc6842919d10c1ae54a3e195
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

Loading…