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

HRID 1098887

Reaktionsgleichung

Reaktionsgleichung von HRID 1098887
[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-e683cd74355d4aa98d5073f3bc8a9998
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143290B2

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