Cesium carbonate → HCID 70817658, Verbindung

HRID 82104

Reaktionsgleichung

Reaktionsgleichung von HRID 82104
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([C:18]([C:20]3[C:28]4[CH:27]=[N:26][CH:25]=[N:24][C:23]=4[NH:22][CH:21]=3)=[O:19])[CH:17]=2)=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:36][C:37]([NH2:39])=[O:38]>CN(C=O)C>[NH2:39][C:37](=[O:38])[CH2:36][N:22]1[C:23]2[N:24]=[CH:25][N:26]=[CH:27][C:28]=2[C:20]([C:18]([C:16]2[CH:17]=[C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:13]=[N:14][CH:15]=2)=[O:19])=[CH:21]1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 708176452-(4-chlorophenyl)-N-[5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylcarbonyl)pyridin-3-yl]acetamide

Produkt 1

HCID 70817658HCID 70817658, VerbindungAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(4-chlorophenyl)-N-[5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylcarbonyl)pyridin-3-yl]acetamide (Example 308, 50 mg, 0.13 mmol) in DMF (1 ml) was added Cs2CO3 (75 mg, 0.23 mmol) followed by 2-bromoacetamide (21.3 mg, 0.154 mmol). The reaction was then stirred at room temperature overnight. The reaction was quenched with water (5 mL) and extracted with EtOAc (3×5 mL). The organics were combined, washed with water (5 mL) then brine (5 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo. Purification by preparative HPLC gave the title compound in 59% yield, 34 mg.

Aufarbeitung

  1. customThe reaction was quenched with water (5 mL)
  2. extractionextracted with EtOAc (3×5 mL)
  3. washwashed with water (5 mL)
  4. dry with materialbrine (5 mL), dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-49952a09578e4a01a44231957fd0b892
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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