Hydrochloric Acid → 1-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}cyclopentanecarboxylic acid

HRID 645977

Reaktionsgleichung

Reaktionsgleichung von HRID 645977
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3([C:29]([O:31]C)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:19][CH2:18]2)=[O:14])[C:5]1=[O:33])([CH3:3])[CH3:2].Cl>C(O)(=O)C>[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH:15][CH2:16][CH:17]2[CH2:18][CH2:19][N:20]([CH2:23][C:24]3([C:29]([OH:31])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:21][CH2:22]2)=[O:14])[C:5]1=[O:33])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 68584479Methyl 1-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}cyclopentanecarboxylate

Produkt 1

HCID 115105321-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}cyclopentanecarboxylic acidAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of Methyl 1-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}cyclopentanecarboxylate (1.33 g, 2.90 mmol, Step 4) in 4N—HCl (6 mL) and acetic acid (6 mL) was stirred at reflux for 18 h. After cooling, the reaction mixture was concentrated and basified with sat. NaHCO3 aq. (100 mL), extracted with CH2Cl2 (150 mL) for three times. The combined extracts were dried over Na2SO4, filtered and concentrated. The residue was chromatographed on a column of silica gel eluted with MeOH/CH2Cl2 (1:10) to give 1.12 g (85%) of title compound as white solid. The crude compound was recrystallized from EtOAc×2 and dried in vacuo at 50° C. for 2 days to give 610 mg of title compound as white crystal.

Aufarbeitung

  1. temperatureat reflux for 18 h
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated
  4. extractionextracted with CH2Cl2 (150 mL) for three times
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on a column of silica gel
  9. washeluted with MeOH/CH2Cl2 (1:10)

Quellen und Nachweise

ORD-Eintrag
ord-7dcfa7e8b4494352ba92e603a4cfb6b2
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705020B2

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