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

HRID 2370936
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2370936
[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
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Komponenten

5

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1ad0aaaa629b442082ea9ef23be19c74
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08710232B2

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