Potassium Carbonate → HCID 58180582, Verbindung

HRID 220358

Reaktionsgleichung

Reaktionsgleichung von HRID 220358
[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:20][CH3:21])[C:9]([C:11]([N:13]([CH:17]3[CH2:19][CH2:18]3)[CH:14]3[CH2:16][CH2:15]3)=[O:12])=[CH:10][C:5]2=[C:4]2[N:22]([CH3:25])[CH:23]=[N:24][C:3]=12.C([N:34]=[C:35]=[S:36])(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].Br.Br[CH2:45][C:46]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][N:49]=1)=O>CC(C)=O>[CH:14]1([N:13]([CH:17]2[CH2:19][CH2:18]2)[C:11]([C:9]2[N:8]([CH2:20][CH3:21])[C:6]3=[N:7][C:2]([NH:1][C:35]4[S:36][CH:45]=[C:46]([C:48]5[CH:53]=[CH:52][CH:51]=[CH:50][N:49]=5)[N:34]=4)=[C:3]4[N:24]=[CH:23][N:22]([CH3:25])[C:4]4=[C:5]3[CH:10]=2)=[O:12])[CH2:16][CH2:15]1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 27762312-Bromo-1-(2-pyridinyl)-1-ethanone hydrobromideHCID 581805034-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

Produkt 1

HCID 58180582HCID 58180582, VerbindungAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 4-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 1J, 70 mg, 0.21 mmol) and benzoyl isothiocyanate (36 μl, 0.27 mmol) in acetone (1 ml) was stirred at room temperature for 1.5 h. The solvent was removed in vacuo, the residue was taken up in EtOH (1.5 ml), and K2CO3 (40 mg, 0.290 mmol) was added. The reaction was heated at 60° C. for 3 h. Upon cooling to room temperature, 2-bromo-1-(pyridin-2-yl)ethanone, hydrobromide (139.4 mg, 0.50 mmol) was added and the reaction heated at 80° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (0-7% MeOH/dichloromethane). Re-purification by preparative HPLC provided 10.2 mg (10% yield) of N,N-dicyclopropyl-6-ethyl-1-methyl-4-(4-(pyridin-2-yl)thiazol-2-ylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide as a brown solid.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. temperatureUpon cooling to room temperature
  3. temperaturethe reaction heated at 80° C. for 24 h
  4. temperatureThe reaction mixture was cooled to room temperature
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-7% MeOH/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-784294f13ca14d49a5ece0fc2b4d2b57
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202881B2

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