Cesium carbonate → HCID 87447416, Verbindung

HRID 390714

Reaktionsgleichung

Reaktionsgleichung von HRID 390714
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]([N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:8].ClC1C=C2C(N=CC=C2)=C2C=1C=CC=N2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:36]1[CH:37]=[CH:38][C:39]([C:42]([F:45])([F:44])[F:43])=[N:40][CH:41]=1.[OH-].[NH4+].O>CN1CCCC1=O>[F:43][C:42]([F:45])([F:44])[C:39]1[N:40]=[CH:41][C:36]([N:3]2[CH:4]=[CH:5][S:1]/[C:2]/2=[N:6]\[C:7]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)=[O:8])=[CH:37][CH:38]=1

Komponenten

7

Edukt 5

HCID 10796Cesium carbonateHCID 778655-Chloro-1,10-phenanthrolineHCID 27611975-Bromo-2-(trifluoromethyl)pyridineHCID 86589665Water ammonium hydroxideHCID 86631924N-1,3-thiazol-2-ylpyrrolidine-1-carboxamide

Produkt 1

HCID 87447416HCID 87447416, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a 4 mL vial charged with a stir bar, N-1,3-thiazol-2-ylpyrrolidine-1-carboxamide (46 mg, 0.23 mmol, Example 32A) was added, followed by copper(I) trifluoromethanesulfonate benzene complex (30 mg, 0.05 mmol), 5-chloro-1,10-phenanthroline (23 mg, 0.09 mmol) and cesium carbonate (100 mg, 0.3 mmol). A loose cap with septum was placed on the vial and the vial was placed under vacuum in a vacuum oven for 30 minutes. The solid mixture was purged with nitrogen gas a couple of times. Then 5-bromo-2-(trifluoromethyl)pyridine (68 mg, 0.3 mmol) dissolved in 1-methyl-2-pyrrolidinone (1.0 mL) was added to the solid mixture. The vial was capped and placed on a heater/stirrer and heated to 120° C. overnight. Then a 1 mL solution of concentrated ammonium hydroxide/water (1:2) was added. The reaction was filtered and concentrated to dryness. The residue was purified by reverse phase HPLC (C18, gradient 10-95% acetonitrile/water/0.1% trifluoroacetic acid) to provide the title compound.

Aufarbeitung

  1. additionIn a 4 mL vial charged with a stir bar
  2. customA loose cap with septum
  3. customThe solid mixture was purged with nitrogen gas a couple of times
  4. additionwas added to the solid mixture
  5. customThe vial was capped
  6. customplaced on a heater/stirrer
  7. filtrationThe reaction was filtered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by reverse phase HPLC (C18, gradient 10-95% acetonitrile/water/0.1% trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-56378088470641529a5f4944003f1830
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383657B2

Verknüpfte Notizen

Wird geladen…