Hydrochloric Acid → HCID 69252172, compound

HRID 2370919Notes

Reaction equation

HRID 2370919 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([C:22]2[N:23]=[CH:24][N:25]([CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:26]=2)(C(OC)=O)[C:10]([O:12]C2CCCC2)=[O:11])=[CH:4][CH:3]=1.Cl>C(O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:22]2[N:23]=[CH:24][N:25]([CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:26]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69252175HCID 69252175, compound

Product 1

HCID 69252172HCID 69252172, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

Cyclopentyl methyl 2-(6-aminopyridin-3-ylmethyl)-2-(1-cyclopentyl-1H-imidazol-4-yl)malonate (0.30 g; 0.57 mmol) was dissolved in absolute ethanol (5 ml). At 0° C., ethanolic HCl was added. The reaction solution was left to stand at 10° C. for 48 h. It was then concentrated under reduced pressure and the residue was taken up in 2N HCl. It was heated in a microwave (3×4 min; 180° C.). This was followed by washing with EA, and the aqueous phase was neutralized with 1N NaOH and then freeze-dried. The residue was taken up in methanol and filtered twice through a cartridge (C18). Concentration of the filtrate under reduced pressure resulted in 0.10 g of 3-(6-aminopyridin-3-yl)-2-(1-cyclopentyl-1H-imidazol-4-yl)-propionic acid.

Workup

  1. waitThe reaction solution was left
  2. concentrationIt was then concentrated under reduced pressure
  3. washby washing with EA
  4. customfreeze-dried
  5. filtrationfiltered twice through a cartridge (C18)
  6. customConcentration of the filtrate under reduced pressure resulted in 0.10 g of 3-(6-aminopyridin-3-yl)-2-(1-cyclopentyl-1H-imidazol-4-yl)-propionic acid

Sources & evidence

ORD record
ord-8eafa7900ad7443fa7274a416eec0618
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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