Cesium carbonate → HCID 178429371, Verbindung

HRID 707377

Reaktionsgleichung

Reaktionsgleichung von HRID 707377
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:12][C@H:13]1[CH2:16][C@H:15]([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][N:25]=[C:20]3[C:19]([CH3:27])([CH3:26])[C:18]2=[O:28])[CH2:14]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][N:5]=2)[CH:10]=[CH:11][C:2]=1[NH:12][C@H:13]1[CH2:16][C@H:15]([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][N:25]=[C:20]3[C:19]([CH3:26])([CH3:27])[C:18]2=[O:28])[CH2:14]1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 51528382-Chloro-1,8-naphthyridineHCID 178429368HCID 178429368, Verbindung

Produkt 1

HCID 178429371HCID 178429371, VerbindungAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-chloro-1,8-naphthyridine (89 mg, 0.54 mmol), 5-(trans-3-aminocyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (100 mg, 0.431 mmol), and cesium carbonate (202 mg, 0.620 mmol) were suspended in dry dimethylformamide (0.86 mL) under nitrogen and heated to 100° C. for 18 h. The mixture was cooled and extracted with ethyl acetate and water. The phases were separated and the organic was dried with magnesium sulfate before evaporating to dryness under reduced pressure. Purification using the ISCO (0-100% EtOAc in hexane), gave the desired 5-(trans-3-((1,8-naphthyridin-2-yl)amino)cyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (32 mg, 0.089 mmol, 21% yield) as a light yellow solid. 1H NMR (300 MHz, CHLOROFORM-d) δ: ppm 1.45 (s, 6 H) 2.42 (ddd, J=13.88, 9.28, 3.29 Hz, 2 H) 3.44-3.62 (m, 2 H) 5.22-5.38 (m, 2 H) 6.71 (d, J=8.92 Hz, 1 H) 7.16 (dd, J=7.82, 4.46 Hz, 1 H) 7.79-7.98 (m, 2 H) 8.11 (q, J=3.12 Hz, 2 H) 8.84 (dd, J=4.38, 1.90 Hz, 1 H).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate and water
  3. customThe phases were separated
  4. dry with materialthe organic was dried with magnesium sulfate
  5. custombefore evaporating to dryness under reduced pressure
  6. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-e3acc8aeba6d42bd852118fa1a6a1195
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174992B2

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