Ethyl isocyanatoacetate → Ethyl n-{[(1s,2r)-2-{[1-(4-fluorophenyl)-1h-indazole-5-yl]oxy}-1-methyl-2-phenylethyl]carbamoyl}glycinate

HRID 13126

Reaktionsgleichung

Reaktionsgleichung von HRID 13126
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@H:19]([CH3:21])[NH2:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:28]([O:30][C:31](=[O:36])[CH2:32][N:33]=[C:34]=[O:35])[CH3:29]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C@@H:19]([NH:20][C:34]([NH:33][CH2:32][C:31]([O:30][CH2:28][CH3:29])=[O:36])=[O:35])[CH3:21])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 76283Ethyl isocyanatoacetateHCID 59339817(alphaS,betaR)-beta-{[1-(4-Fluorophenyl)-1H-indazole-5-yl]oxy}-alpha-methylbenzeneethanamine

Produkt 1

HCID 44594899Ethyl n-{[(1s,2r)-2-{[1-(4-fluorophenyl)-1h-indazole-5-yl]oxy}-1-methyl-2-phenylethyl]carbamoyl}glycinateAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(αS,βR)-β-{[1-(4-Fluorophenyl)-1H-indazole-5-yl]oxy}-α-methylbenzeneethanamine (80 mg, 0.22 mmol), as described in Example 1, is dissolved in 1.42 mL dichloromethane and ethylisocyanatoacetate (28.6 mg, 0.22 mmol) is dropwise added. After stirring for 45 min at r.t. the solvent is removed and the residue purified by chromatography (silicagel, eluents: hexane/ethylacetate). 85.4 mg (78.6%) of the title compound are obtained.

Aufarbeitung

  1. customis removed
  2. customthe residue purified by chromatography (silicagel, eluents: hexane/ethylacetate)

Quellen und Nachweise

ORD-Eintrag
ord-82aaeec6ede14f6d8c1b69dc920b0408
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

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