Potassium Carbonate → 2-methyl-5-(3-morpholin-4-ylpropoxy)-3-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}pyrazolo[1,5-a]pyridine

HRID 1530069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1530069
[CH3:1][C:2]1[C:11]([C:12]2[S:13][C:14]([C:23]3[N:27]=[CH:26][N:25]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][O:29]4)[N:24]=3)=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=2)=[C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][N:4]2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:41][CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.C(=O)(O)[O-].[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[C:11]([C:12]2[S:13][C:14]([C:23]3[N:27]=[CH:26][N:25]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][O:29]4)[N:24]=3)=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=2)=[C:5]2[CH:6]=[C:7]([O:10][CH2:41][CH2:42][CH2:43][N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)[CH:8]=[CH:9][N:4]2[N:3]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 958344-(3-Chloropropyl)morpholineHCID 516892Sodium BicarbonateHCID 178433751HCID 178433751, Verbindung

Produkt 1

HCID 668564252-methyl-5-(3-morpholin-4-ylpropoxy)-3-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}pyrazolo[1,5-a]pyridineAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a suspension of 2-methyl-3-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}pyrazolo[1,5-a]pyridin-5-ol (100 mg, 0.218 mmol) obtained in Example 31-B-(i) and potassium carbonate (60.3 mg, 0.436 mmol) in DMF (4 mL), was added 4-(3-chloropropyl)morpholine (71.3 mg, 0.436 mmol) obtained above and the mixture was stirred for 5 h at 60° C. To the reaction mixture, were added EtOAc (20 mL) and saturated aqueous solution of sodium bicarbonate (15 mL). The organic layer was separated and then aqueous layer was extracted with EtOAc (5 mL). The combined organic layers were washed with brine (5 mL) and then dried over anhydrous sodium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/hexane=30/70→60/40) to give the title compound (128 mg, quant) as a colorless solid

Aufarbeitung

  1. customobtained above and the mixture
  2. customThe organic layer was separated
  3. extractionaqueous layer was extracted with EtOAc (5 mL)
  4. washThe combined organic layers were washed with brine (5 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customInsoluble materials were removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (EtOAc/hexane=30/70→60/40)

Quellen und Nachweise

ORD-Eintrag
ord-de7e05e52e87441db857aae12b85e35b
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090601B2

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