rac-tert-butyl N-((1R,3S)-3-aminocyclohexyl)carbamate → tert-butyl N-[(1R,3S)-3-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]cyclohexyl]carbamate

HRID 526951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 526951
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.[Cl:16][C:17]1[CH:18]=[C:19]2[C:25]([C:26]3[N:31]=[C:30](S(C)=O)[C:29]([F:35])=[CH:28][N:27]=3)=[CH:24][N:23]([S:36]([C:39]3[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[C:20]2=[N:21][CH:22]=1>C1COCC1>[Cl:16][C:17]1[CH:18]=[C:19]2[C:25]([C:26]3[N:31]=[C:30]([NH:1][C@H:2]4[CH2:7][CH2:6][CH2:5][C@@H:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3]4)[C:29]([F:35])=[CH:28][N:27]=3)=[CH:24][N:23]([S:36]([C:39]3[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[C:20]2=[N:21][CH:22]=1

Komponenten

4

Edukt 2

HCID 59710757rac-tert-butyl N-((1R,3S)-3-aminocyclohexyl)carbamateHCID 672853215-Chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine

Produkt 1

HCID 68007892tert-butyl N-[(1R,3S)-3-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]cyclohexyl]carbamateAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

tert-Butyl N-[(1R,3S)-3-aminocyclohexyl]carbamate, 20a, (0.15 g, 0.70 mmol) and 5-chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine, 1a, (0.49 g, 1.05 mmol) were dissolved in THF (30 mL) and allowed to stir at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was purified by two rounds of silica gel chromatography—first with (0%-10% MeOH/CH2Cl2) second with (10%-50% EtOAc/hexanes) to provide tert-butyl N-[(1R,3S)-3-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]cyclohexyl]carbamate (20b) (330 mg, 38%).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by two rounds of silica gel chromatography—first with (0%-10% MeOH/CH2Cl2) second with (10%-50% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d669e9d464344c2db219be7750e34be4
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345708B2

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