Triethylamine → Methyl 4-(5-{(1R,2S)-2-[(2-furylcarbonyl)amino]-1-phenylpropoxy}-1H-indazole-1-yl)benzoate

HRID 13141

Reaktionsgleichung

Reaktionsgleichung von HRID 13141
[NH2:1][C@@H:2]([CH3:30])[C@@H:3]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)[N:9]=[CH:8]2.C(N(CC)CC)C.[O:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[C:43](Cl)=[O:44]>ClCCl>[O:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[C:43]([NH:1][C@@H:2]([CH3:30])[C@@H:3]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)[N:9]=[CH:8]2)=[O:44]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 66812703Methyl 4-{5-[(1R,2S)-2-amino-1-phenylpropoxy]-1H-indazole-1-yl}benzoate

Produkt 1

HCID 44515372Methyl 4-(5-{(1R,2S)-2-[(2-furylcarbonyl)amino]-1-phenylpropoxy}-1H-indazole-1-yl)benzoateAusbeute 48,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Methyl 4-{5-[(1R,2S)-2-amino-1-phenylpropoxy]-1H-indazole-1-yl}benzoate (64.3 mg, 0.16 mmol) is dissolved in 6.1 mL of dichloromethane. Triethylamine (0.053 mL, 0.38 mmol) and 2-furoylchloride (20.9 mg, 0.16 mmol) are added. After 4 h stirring at r.t. the reaction mixture is diluted with dichloromethane, washed with water and brine and dried over Na2SO4. The reaction mixture is filtered, the solvent evaporated and the residue purified by chromatography (silicagel, eluents: ethyl acetate/hexane). 38.2 mg (48.1%) of the title compound are obtained.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationThe reaction mixture is filtered
  4. customthe solvent evaporated
  5. customthe residue purified by chromatography (silicagel, eluents: ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3aac0ecc06624f02a36622bbe59ba2f9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

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