Diisopropylethylamine → 2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-((1S,3R)-3-isocyanato-3-methylcyclohexyl)pyrimidin-4-amine

HRID 527032

Reaktionsgleichung

Reaktionsgleichung von HRID 527032
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][C@@:20]([CH3:27])(C(O)=O)[CH2:19]4)[C:14]([F:28])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.N(P([O:41][C:42]1C=CC=CC=1)(OC1C=CC=CC=1)=O)=[N+]=[N-].C([N:50](C(C)C)C(C)C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][C@:20]([N:50]=[C:42]=[O:41])([CH3:27])[CH2:19]4)[C:14]([F:28])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 123414Diphenylphosphoryl azideHCID 68007671(1R,3S)-3-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-1-methylcyclohexanecarboxylic acid

Produkt 1

HCID 866674372-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-((1S,3R)-3-isocyanato-3-methylcyclohexyl)pyrimidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of (1R,3S)-3-[[2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-yl]amino]-1-methyl-cyclohexanecarboxylic acid, 826, (0.100 g, 0.216 mmol) and (azido(phenoxy)phosphoryl)oxybenzene (0.093 mL, 0.432 mmol) in 10 mL of toluene was added 1 mL of N-ethyl-N-isopropyl-propan-2-amine. The reaction was warmed to reflux overnight. The mixture was concentrated to dryness and the residue was purified by silica gel chromatography (EtOAc), yielding 40 mg of desired product as a white foam.

Aufarbeitung

  1. temperatureThe reaction was warmed
  2. temperatureto reflux overnight
  3. concentrationThe mixture was concentrated to dryness
  4. customthe residue was purified by silica gel chromatography (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-949e1de99e9941baaec4e4045766dfaa
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345708B2

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