Potassium Carbonate → (4-Morpholin-4-yl-phenyl)-[8-(2-phenoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]-amine

HRID 570604

Reaktionsgleichung

Reaktionsgleichung von HRID 570604
Cl[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:14][CH:13]=3)[N:10]=2)[CH:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O:59]([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=1B(O)O)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>C(O)C.C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:18]1([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:9]3[N:10]=[C:3]4[C:2]([C:61]5[CH:62]=[CH:63][CH:64]=[CH:65][C:60]=5[O:59][C:66]5[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=5)=[N:7][CH:6]=[CH:5][N:4]4[N:8]=3)=[CH:13][CH:14]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 2773559(2-Phenoxyphenyl)boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl2×HCID 866943398-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl-(4-morpholin-4-yl-phenyl)-amine

Produkt 1

HCID 56846952(4-Morpholin-4-yl-phenyl)-[8-(2-phenoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 21863594Toluene ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of (8-chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl-(4-morpholin-4-yl-phenyl)-amine (0.15 g, 0.45 mmol, 1 eq) in a mixture of ethanol:toluene (1:4) (10 ml) is taken in a dry pressure tube, palladium acetate (0.01 g, 0.045 mmol, 0.1 eq), anhydrous potassium carbonate (0.125 g, 0.90 mmol, 2 eq), 2-dicyclo-hexylphosphino-2′,6′-dimethoxybiphenyl, S-Phos (0.027 g, 0.06 mmol, 0.13 eq) and 2-phenoxyphenylboronic acid (0.19 g, 0.90 mmol, 2 eq) are added and the reaction mixture is degasified with nitrogen. The reaction mixture is heated to 120° C. for 1 hour. The reaction mixture is concentrated and the residue is taken in 25% methanol in dichloromethane (50 ml) and filtered through celite to remove the inorganics and the filtrate is concentrated and purified by silica column using (230-400) mesh to get the product as pale yellow solid.

Aufarbeitung

  1. customis taken in a dry pressure tube
  2. concentrationThe reaction mixture is concentrated
  3. filtrationfiltered through celite
  4. customto remove the inorganics
  5. concentrationthe filtrate is concentrated
  6. custompurified by silica column

Quellen und Nachweise

ORD-Eintrag
ord-fce8bfcdb2ea4b4a93a0f660b2257943
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023851B2

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