Potassium Carbonate → N-(4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)benzo[d]oxazol-2-amine

HRID 1854351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1854351
[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C:23]45[CH2:30][CH2:29][C:26]([NH2:31])([CH2:27][CH2:28]4)[CH2:25][CH2:24]5)=[N:21][N:22]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].Cl[C:33]1[O:34][C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C:23]45[CH2:30][CH2:29][C:26]([NH:31][C:33]6[O:34][C:35]7[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=7[N:37]=6)([CH2:27][CH2:28]4)[CH2:25][CH2:24]5)=[N:21][N:22]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 119862-ChlorobenzoxazoleHCID 580097794-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[2.2.2]octan-1-amine

Produkt 1

HCID 58009924N-(4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)benzo[d]oxazol-2-amineAusbeute 102,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A pear shaped flask was charged with 4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[2.2.2]octan-1-amine (0.20 g, 0.46 mmol, Example #7, Step B) and 2-chlorobenzo[d]oxazole (0.18 g, 1.1 mmol, TCI) in DMF (5.0 mL). To the suspension was added K2CO3 (0.16 g, 1.1 mmol) and the mixture was heated to about 65° C. for about 8.5 h. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The residue was dissolved into EtOAc (25 mL) and washed with water and brine (25 mL each). The organic solution was dried over anhydrous MgSO4, filtered, and concentrated to dryness under reduced pressure to give N-(4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)benzo[d]oxazol-2-amine (0.26 g, 95%, 95% purity by ELSD): LC/MS (Table 2, Method d) Rt=1.48 min; MS m/z: 554 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved into EtOAc (25 mL)
  4. washwashed with water and brine (25 mL each)
  5. dry with materialThe organic solution was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3b2ae0a929674f5788622b7fadd93978
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962629B2

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