Pyridine → Methyl 4-[6-(cyclopentyloxycarbonyl)amino-3-methoxyindazol-1-ylmethyl]-3-methoxybenzoate

HRID 1742325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1742325
Cl[C:2]([O:4][CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:3].[NH2:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([O:33][CH3:34])=[N:16][N:17]2[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[O:31][CH3:32])=[CH:13][CH:12]=1.N1C=CC=CC=1>ClCCl.C(OCC)(=O)C>[CH:5]1([O:4][C:2]([NH:10][C:11]2[CH:19]=[C:18]3[C:14]([C:15]([O:33][CH3:34])=[N:16][N:17]3[CH2:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=3[O:31][CH3:32])=[CH:13][CH:12]=2)=[O:3])[CH2:9][CH2:8][CH2:7][CH2:6]1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 2735892Cyclopentyl chloroformateHCID 23365880Methyl 4-[6-amino-3-methoxyindazol-1-ylmethyl]-3-methoxybenzoate

Produkt 1

HCID 23365908Methyl 4-[6-(cyclopentyloxycarbonyl)amino-3-methoxyindazol-1-ylmethyl]-3-methoxybenzoateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Cyclopentyl chloroformate (0.17 ml.) was added to a cooled (-20° C.) solution of methyl 4-[6amino-3-methoxyindazol-1-ylmethyl]-3-methoxybenzoate (S) (0.381 g.) and pyridine (0.11 ml.) in dichloromethane (3.0 ml.). After warming to ambient temperature, the mixture was diluted with ethyl acetate, and washed with hydrochloric acid (1N), water, brine, dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel (56 g.), eluting with 5:95 v/v ethyl acetate: dichloromethane, to give the title compound (0.365 g., 75%) as an oil, with satisfactory NMR spectral data.

Aufarbeitung

  1. washwashed with hydrochloric acid (1N), water, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by flash chromatography on silica gel (56 g.)
  5. washeluting with 5:95 v/v ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ea406e1a2b8e4cadb1e846b40518f256
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05338734

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