Diisopropylethylamine → HCID 178461213, Verbindung

HRID 81217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81217
[NH:1]1[CH2:6][CH2:5][NH:4][C@@H:3]2[CH2:7][CH2:8][CH2:9][C@@H:2]12.Br[C:11]1[N:28]([CH2:29][C@H:30]2[CH2:35][CH2:34][C@H:33]([CH3:36])[CH2:32][CH2:31]2)[C:14]2[C:15]([C:21]3[CH:22]=[N:23][CH:24]=[C:25]([Cl:27])[CH:26]=3)=[N:16][C:17]([C:19]#[N:20])=[CH:18][C:13]=2[N:12]=1.[F-].[K+].CCN(C(C)C)C(C)C>CCOC(C)=O.CS(C)=O>[Cl:27][C:25]1[CH:26]=[C:21]([C:15]2[C:14]3[N:28]([CH2:29][C@H:30]4[CH2:35][CH2:34][C@H:33]([CH3:36])[CH2:32][CH2:31]4)[C:11]([N:1]4[CH2:6][CH2:5][NH:4][C@@H:3]5[CH2:7][CH2:8][CH2:9][C@@H:2]45)=[N:12][C:13]=3[CH:18]=[C:17]([C:19]#[N:20])[N:16]=2)[CH:22]=[N:23][CH:24]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 522689Potassium FluorideHCID 86724561(4aR,7aR)-octahydro-1H-cyclopenta[b]pyrazineHCID 178461197HCID 178461197, Verbindung

Produkt 1

HCID 178461213HCID 178461213, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a microwave vial was added (4aR,7aR)-octahydro-1H-cyclopenta[b]pyrazine (Preparative Example 5.2,295 mg, 2.338 mmol), 2-bromo-4-(5-chloropyridin-3-yl)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile (Preparative Example 3.1, 800 mg, 1.799 mmol), potassium fluoride (209 mg, 3.60 mmol), DMSO (8 ml), and DIEA (0.942 ml, 5.40 mmol). The reaction vial was capped and heated to 100° C. overnight. The mixture was then cooled to room temperature and diluted with EtOAc. The solution was washed with water and brine, dried over sodium sulfate, filtered, and concentrated to give crude 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(4aR,7aR)-octahydro-1H-cyclopenta[b]pyrazin-1-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ESI calc'd. for C27H32ClN7 [M+H]+ 490. found 490.

Aufarbeitung

  1. customThe reaction vial was capped
  2. temperatureThe mixture was then cooled to room temperature
  3. washThe solution was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f7c24fb0544f4accbbe4322981edbc39
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846657B2

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