Hydrochloric Acid → 3-(6-Aminopyridin-3-yl)-2-{1-[2-(1-diphenylacetylpiperidin-4-yl)ethyl]-1H-imidazol-4-yl}propionic acid

HRID 2370936Notes

Reaction equation

HRID 2370936 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][N:18]([CH2:20][CH2:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28](=[O:42])[CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:24][CH2:23]3)[CH:19]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][N:18]([CH2:20][CH2:21][CH:22]3[CH2:23][CH2:24][N:25]([C:28](=[O:42])[CH:29]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH2:26][CH2:27]3)[CH:19]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67415723ethyl 3-(6-aminopyridin-3-yl)-2-{1-[2-(1-diphenylacetylpiperidin-4-yl)ethyl]-1H-imidazol-4-yl}propionate

Product 1

HCID 115774213-(6-Aminopyridin-3-yl)-2-{1-[2-(1-diphenylacetylpiperidin-4-yl)ethyl]-1H-imidazol-4-yl}propionic acidYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-(6-aminopyridin-3-yl)-2-{1-[2-(1-diphenylacetylpiperidin-4-yl)ethyl]-1H-imidazol-4-yl}propionate (71 mg; 0.12 mmol) was dissolved in absolute ethanol (600 μl). 1N NaOH (128 μl; 0.12 mmol) was added thereto. The reaction mixture was stirred at RT for 16 h. It was then neutralized with 1N HCl (128 μl; 0.12 mmol) and concentrated under reduced pressure. It was taken up in methanol and filtered through a C18 column. The methanol was removed and acetonitrile was added and decanted twice, and the residue was then triturated with diethyl ether. The precipitate was filtered off and dried under high vacuum at 40° C. 3-(6-Aminopyridin-3-yl)-2-{1-[2-(1-diphenylacetylpiperidin-4-yl)ethyl]-1H-imidazol-4-yl}propionic acid (50 mg; 0.09 mmol) was obtained as a colorless solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationfiltered through a C18 column
  3. customThe methanol was removed
  4. additionacetonitrile was added
  5. customdecanted twice
  6. customthe residue was then triturated with diethyl ether
  7. filtrationThe precipitate was filtered off
  8. customdried under high vacuum at 40° C

Sources & evidence

ORD record
ord-1ad0aaaa629b442082ea9ef23be19c74
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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