1,1'-Carbonyldiimidazole → HCID 59683283, Verbindung

HRID 447778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 447778
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:11][CH2:10]2)=[CH:4][C:3]=1[NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C1N=CN([C:31](N2C=NC=C2)=[O:32])C=1>O1CCCC1>[CH:9]1([C:5]2[CH:6]=[C:7]([F:8])[C:2]3[NH:1][C:31](=[O:32])[N:12]([CH:13]4[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]4)[C:3]=3[CH:4]=2)[CH2:11][CH2:10]1

Komponenten

4

Edukt 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 596832651,1-Dimethylethyl 4-[(2-amino-5-cyclopropyl-3-fluorophenyl)amino]-1-piperidinecarboxylate

Produkt 1

HCID 59683283HCID 59683283, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl 4-[(2-amino-5-cyclopropyl-3-fluorophenyl)amino]-1-piperidine-carboxylate (D27, 0.80 mmol, 280 mg) was dissolved in 4 ml of tetrahydrofuran and CDI (1,1′-(oxomethanediyl)bis-1H-imidazole) (2.5 eq., 2.0 mmol, 0.33 g) at room temperature and the mixture was stirred at 50° C. for one overnight under argon. Extra CDI (1 eq., 0.13 g, 0.80 mmol) was added and the mixture was refluxed for two extra hours. The mixture was cooled to room temperature and the solvent was evaporated to afford the crude compound which was purified by chromatography (ethyl acetate (50)-n-hexane (50)) to yield the title compound, 102 mg, 36%, M−−H=374.

Aufarbeitung

  1. temperaturethe mixture was refluxed for two extra hours
  2. customthe solvent was evaporated
  3. customto afford the crude compound which
  4. customwas purified by chromatography (ethyl acetate (50)-n-hexane (50))

Quellen und Nachweise

ORD-Eintrag
ord-31e4022220ac4886b885c3cebeea2491
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481566B2

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