Potassium Carbonate → Cyclopropyl-(5''-ethynyl-[2,2';4',3'']terpyridin-6'-yl)-amine

HRID 1798513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798513
[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[CH:8]=[C:7]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([C:23]#[C:24][Si](C)(C)C)[CH:22]=3)[CH:6]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO.CCOC(C)=O>[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[CH:8]=[C:7]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([C:23]#[CH:24])[CH:22]=3)[CH:6]=2)[CH2:2][CH2:3]1

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 68947114Cyclopropyl-(5''-trimethylsilanylethynyl-[2,2';4',3'']terpyridin-6'-yl)-amine

Produkt 1

HCID 86633651Cyclopropyl-(5''-ethynyl-[2,2';4',3'']terpyridin-6'-yl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Cyclopropyl-(5″-trimethylsilanylethynyl-[2,2′;4′,3″]terpyridin-6′-yl)-amine (Example 2.128, step1) (1 eq, 0.127 mmol, 49 mg) is dissolved in MeOH (2 ml) and potassium carbonate is added (2 eq, 0.255 mmol, 35 mg). The reaction mixture is dissolved in EtOAc and washed with water. The organic layer is washed with brine, dried over drying agent MgSO4, filtered and the organic solvent is reduced in vacuo. The crude residue is purified by reverse phase column chromatography (Isolute™ C18, 0-20% acetonitrile in water—0.1% TFA). The appropriate fractions by HPLC are combined and concentrated in vacuo. The resulting residue is dissolved in MeOH and loaded onto a SCX-2 cartridge eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are combined, concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 313.

Aufarbeitung

  1. washwashed with water
  2. washThe organic layer is washed with brine
  3. customdried
  4. dry with materialover drying agent MgSO4
  5. filtrationfiltered
  6. customThe crude residue is purified by reverse phase column chromatography (Isolute™ C18, 0-20% acetonitrile in water—0.1% TFA)
  7. concentrationconcentrated in vacuo
  8. dissolutionThe resulting residue is dissolved in MeOH
  9. washeluting with MeOH
  10. concentrationconcentrated in vacuo
  11. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7cb0218a28bb47e693f9f4cb5729e5ee
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343966B2

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