Potassium Carbonate → HCID 71515487, Verbindung

HRID 1466214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1466214
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][NH:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:26]([CH3:27])=[N:25][N:24]([CH3:28])[C:12]2=[N:13][C:14]=1[N:15]([CH2:20][CH:21]1[CH2:23][CH2:22]1)[CH2:16][CH:17]1[CH2:19][CH2:18]1.Cl[C:39]1[N:44]=[CH:43][C:42]([C:45](=[O:47])[CH3:46])=[CH:41][N:40]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:17]1([CH2:16][N:15]([CH2:20][CH:21]2[CH2:23][CH2:22]2)[C:14]2[N:13]=[C:12]3[N:24]([CH3:28])[N:25]=[C:26]([CH3:27])[C:11]3=[CH:10][C:9]=2[CH2:8][N:7]([CH2:6][C:5]2[CH:29]=[C:30]([C:32]([F:34])([F:35])[F:33])[CH:31]=[C:3]([C:2]([F:36])([F:1])[F:37])[CH:4]=2)[C:39]2[N:44]=[CH:43][C:42]([C:45](=[O:47])[CH3:46])=[CH:41][N:40]=2)[CH2:18][CH2:19]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 137157421-(2-Chloropyrimidin-5-yl)ethan-1-oneHCID 894804125-(((3,5-bis(trifluoromethyl)benzyl)amino)methyl)-N,N-bis(cyclopropylmethyl)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-amine

Produkt 1

HCID 71515487HCID 71515487, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

5-(((3,5-bis(trifluoromethyl)benzyl)amino)methyl)-N,N-bis(cyclopropylmethyl)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-amine (0.761 mmol, 0.400 g) in DMF was treated with 1-(2-chloropyrimidin-5-yl)ethanone (0.761 mmol, 0.119 g) and K2CO3 (2.283 mmol, 0.315 g). The reaction mixture was stirred at 60-70° C. for 12-16 h. The reaction mixture was then extracted with EtOAc. The combined organic layer was washed with water and brine solution, dried over sodium sulphate, concentrated under reduced pressure and purified by column chromatography using silica gel and 50% EtOAc in petroleum ether as eluent to get the title compound.

Aufarbeitung

  1. extractionThe reaction mixture was then extracted with EtOAc
  2. washThe combined organic layer was washed with water and brine solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d53933d784e443bfad8d35c5125edda2
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000007B2

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