Potassium Carbonate → (S)-tert-butyl (1-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-5-(3-carbamoyl-4-fluorophenyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

HRID 2170348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2170348
[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C@@H:15]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:16][C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=3)[C:12](Br)=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1.[C:34]([C:37]1[CH:38]=[C:39](B(O)O)[CH:40]=[CH:41][C:42]=1[F:43])(=[O:36])[NH2:35].C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1.CC(O)C.O>[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C@@H:15]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:16][C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=3)[C:12]([C:39]3[CH:40]=[CH:41][C:42]([F:43])=[C:37]([C:34](=[O:36])[NH2:35])[CH:38]=3)=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 44717530(3-Carbamoyl-4-fluorophenyl)boronic acidHCID 90290212(S)-tert-butyl (1-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-5-bromopyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

Produkt 1

HCID 90290213(S)-tert-butyl (1-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-5-(3-carbamoyl-4-fluorophenyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 66631872toluene IPA waterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a microwave tube were charged with compound 23C (52 mg, 0.1 mmol), (3-carbamoyl-4-fluorophenyl)boronic acid (27 mg, 0.15 mmol), K2CO3 (41 mg, 0.3 mmol), Pd(dppf)Cl2 (5 mg). To the mixture was added 2 mL of Toluene/2-propanol/H2O (3/1/1). The mixture was heated up to 120° C. for 20 min in a Microwave Synthesizer. The mixture was partitioned between ethyl acetate and water. The organic layer was separated and concentrated to afford crude product used for next step without further purification. MS (m/z) 582.73 [M+H]+.

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. customto afford crude product
  5. customused for next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-aeea0dfc57894ec59b56e49d4d221f2f
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09050344B2

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