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

HRID 1086560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1086560
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-[6-amino-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-188a3292df464da08c36707642d45ff6
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05030643

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