Ethanol → HCID 25261906, Verbindung

HRID 383285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 383285
C([O-])([O-])=O.[Cs+].[Cs+].[CH2:7]([OH:9])[CH3:8].Cl[C:11]1[CH:16]=[C:15]([C:17]2[N:21]3[CH:22]=[C:23]([NH:26][CH:27]4[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]4)[CH:24]=[CH:25][C:20]3=[N:19][CH:18]=2)[CH:14]=[CH:13][N:12]=1>CS(C)=O.O>[CH2:7]([O:9][C:13]1[CH:14]=[C:15]([C:17]2[N:21]3[CH:22]=[C:23]([NH:26][CH:27]4[CH2:28][CH2:29][CH:30]([OH:33])[CH2:31][CH2:32]4)[CH:24]=[CH:25][C:20]3=[N:19][CH:18]=2)[CH:16]=[CH:11][N:12]=1)[CH3:8]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 10796Cesium carbonateHCID 252619024-[3-(2-Chloro-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino]-cyclohexanol

Produkt 1

HCID 25261906HCID 25261906, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Cs2CO3 (5 eq, 1.45 mmol, 480 mg) and 4A molecular sieves (400 mg) are stirred in a mixture of DMSO (5 ml) and ethanol (5 eq 0.8 ml). To this suspension is added [4-[3-(2-chloro-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino]-cyclohexanol (Example 2.1) (1 eq, 100 mg, 0.29 mmol). The reaction is heated at 120° C. for 16 hours. The mixture is diluted with H2O (20 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo to give a blue oil. The residue is purified by flash chromatography on silica eluting with 0-10% methanol in EtOAc The resulting residue is loaded onto a SCX-2 cartridge (resin loading 0.67 mmol/g) eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+=353

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organic portions are washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a blue oil
  6. customThe residue is purified by flash chromatography on silica eluting with 0-10% methanol in EtOAc The resulting residue
  7. washeluting with MeOH
  8. concentrationThe methanolic ammonia fractions are concentrated in vacuo
  9. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e3902bc4856d42dbb7c16638aa124767
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367662B2

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