Potassium Carbonate → 5-[7-(2-Chloro-pyridin-4-yl)-imidazo[1,2-c]pyrimidin-5-yl]-(1S,4S)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

HRID 729506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 729506
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([Cl:17])[CH:12]=2)[N:3]=1.[C:18]([N:25]1[CH2:30][C@@H:29]2[CH2:31][CH:26]1[CH2:27][NH:28]2)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C([O-])([O-])=O.[K+].[K+].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[C:21]([O:20][C:18]([N:25]1[CH2:30][C@@H:29]2[CH2:31][C@H:26]1[CH2:27][N:28]2[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([Cl:17])[CH:12]=2)[N:3]=1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 45073266(S)-N-Boc-2,5-Diaza-bicyclo[2.2.1]heptaneHCID 578326715-chloro-7-(2-chloro-4-pyridinyl)-Imidazo[1,2-c]pyrimidine

Produkt 1

HCID 866002915-[7-(2-Chloro-pyridin-4-yl)-imidazo[1,2-c]pyrimidin-5-yl]-(1S,4S)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To a 100 mL RBF was added 5-chloro-7-(2-chloro-pyridin-4-yl)-imidazo[1,2-c]pyrimidine (2.0 g, 7.6 mmol), 20 mL NMP, (S)—N-Boc-2,5-Diaza-bicyclo[2.2.1]heptane (1.6 g, 8.3 mmol), K2CO3 (1.05 g, 7.6 mmol) and DIEA (1.3 mL, 7.6 mmol). The mixture was stirred at rt under nitrogen for 15 h, and all starting material was converted. The reaction mixture was added to a 100 mL ice water slowly, and a white solid was precipitated out. The precipitate was filtrated and washed with 50 mL water, and further purified by flash chromatograph. The title compound was obtained. MS (ES+):427 (M+H)+.

Aufarbeitung

  1. customa white solid was precipitated out
  2. filtrationThe precipitate was filtrated
  3. washwashed with 50 mL water
  4. customfurther purified by flash chromatograph

Quellen und Nachweise

ORD-Eintrag
ord-6bb04963d6be4be482797bb5e56a7413
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582631B2

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