Triethylamine → N-[(1S,2R)-1-Methyl-2-phenyl-2-{[1-(4-pyridyl)-1H-indazole-5-yl]oxy}ethyl]furan-2-carboxamide

HRID 13137

Reaktionsgleichung

Reaktionsgleichung von HRID 13137
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][C@H:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C@H:18]([CH3:20])[NH2:19])=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[O:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[C:39](Cl)=[O:40]>ClCCl>[CH3:20][C@H:18]([NH:19][C:39]([C:35]1[O:34][CH:38]=[CH:37][CH:36]=1)=[O:40])[C@@H:17]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[O:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)[N:8]=[CH:9]2

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 67977300(alphaS,betaR)-beta-{[1-(4-Pyridyl)-1H-indazole-5-yl]oxy}-alpha-methylbenzeneethanamine

Produkt 1

HCID 59339672N-[(1S,2R)-1-Methyl-2-phenyl-2-{[1-(4-pyridyl)-1H-indazole-5-yl]oxy}ethyl]furan-2-carboxamideAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(αS,βR)-β{[1-(4-Pyridyl)-1H-indazole-5-yl]oxy}-α-methylbenzeneethanamine (64.3 mg, 0.19 mmol) is dissolved in 7.1 mL of dichloromethane. Triethylamine (0.062 mL, 0.45 mmol) and 2-furoylchloride (24.3 mg, 0.19 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). 53.7 mg (65.6%) 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-2c370ba6baa846c096844a985d05c8ba
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

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