Methanesulfonic Acid → 2,3-Dimethyl-8-(2-ethyl-4-fluoro-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide mesylate

HRID 427488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 427488
[S:1]([OH:5])(=[O:4])(=[O:3])[CH3:2].[NH2:6][C:7]1[C:8]2[N:9]([C:16]([CH3:20])=[C:17]([CH3:19])[N:18]=2)[CH:10]=[C:11]([C:13]([NH2:15])=[O:14])[CH:12]=1.[CH2:21]([C:23]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([CH3:32])[C:24]=1[CH2:25]Cl)[CH3:22].C(N(C(C)C)CC)(C)C.CS(O)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.CO.C(O)C.O.C(Cl)Cl.CN(C)C=O>[S:1]([OH:5])(=[O:4])(=[O:3])[CH3:2].[CH3:19][C:17]1[N:18]=[C:8]2[C:7]([NH:6][CH2:25][C:24]3[C:27]([CH3:32])=[CH:28][C:29]([F:31])=[CH:30][C:23]=3[CH2:21][CH3:22])=[CH:12][C:11]([C:13]([NH2:15])=[O:14])=[CH:10][N:9]2[C:16]=1[CH3:20]

Komponenten

11

Edukt 5

HCID 6395Methanesulfonic Acid2×HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 121489192-Ethyl-4-fluoro-6-methylbenzylchlorideHCID 183574358-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide mesylate

Produkt 1

HCID 183574452,3-Dimethyl-8-(2-ethyl-4-fluoro-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide mesylateAusbeute 23,4 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

8-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide mesylate (0.7 g, 1.9 mmol), 2-ethyl-4-fluoro-6-methylbenzylchloride (0.26 g, 1.9 mmol) and diisopropylethylamin (0.54 g, 4.2 mmol) were added to dimethylformamide (5 ml) and stirred at room temperature for 1 h. Methylene chloride and water were added to the reaction mixture, the organic layer was separated, dried and evaporated under reduced pressure. The residue was solved in ethylacetate and ethanol and metanesulfonic acid (0.2 g, 2 mmol) was added. The product was filtred off and was solved in methylene chloride:methanol (2:1) and an excess of potassium carbonate. The solids were filtred off and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride:methanol (10:1) as eluent. The residue was solved in ethylacetate and methansulfonic acid (0.04 g, 0.4 mmol) was added. The salt was filtred off to give 0.2 g (23%) of the title compound.

Aufarbeitung

  1. customthe organic layer was separated
  2. customdried
  3. customevaporated under reduced pressure
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-22b242024f4a445bbb8580cd55db0e91
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313137B1

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