Hydrochloric Acid → 4-((4-((((3-Isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl)amino)methyl)piperidin-1-yl)methyl)tetrahydro-2H-pyran-4-carboxylic acid

HRID 645968

Reaktionsgleichung

Reaktionsgleichung von HRID 645968
[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:30]([O:32]C(C)(C)C)=[O:31])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH2:19][CH2:18]2)=[O:14])[C:5]1=[O:37])([CH3:3])[CH3:2].Cl>C1COCC1>[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:30]([OH:32])=[O:31])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[CH2:21][CH2:22]2)=[O:14])[C:5]1=[O:37])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 68584353tert-butyl 4-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate

Produkt 1

HCID 117122634-((4-((((3-Isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl)amino)methyl)piperidin-1-yl)methyl)tetrahydro-2H-pyran-4-carboxylic acidAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of tert-butyl 4-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate (3.67 g, 7.13 mmol, step 6) in THF (80 mL) was added conc. HCl (40 mL) at 0° C. and the resulting mixture was stirred for 20 h at room temperature. The mixture was concentrated to remove the solvent and the residue was poured into sat. NaHCO3 aq. The mixture was extracted with CH2Cl2 for three times and the organic layer was dried over Na2SO4. Removal of the solvent gave a residue, which was chromatographed on a column of silica gel eluting MeOH/CH2Cl2 (1:10) to give 3.01 g (92%) of the title compound. The product was recrystalized from THF to give the titled compound (0.893 g) as white crystals.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customto remove the solvent
  3. additionthe residue was poured into sat. NaHCO3 aq. The mixture
  4. extractionwas extracted with CH2Cl2 for three times
  5. dry with materialthe organic layer was dried over Na2SO4
  6. customRemoval of the solvent
  7. customgave a residue, which
  8. customwas chromatographed on a column of silica gel
  9. washeluting MeOH/CH2Cl2 (1:10)

Quellen und Nachweise

ORD-Eintrag
ord-488ec6c26ac448d3932f329b8f15eee2
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705020B2

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