Potassium Iodide → 2,3-Dimethyl-8-(2,6-dimethyl-4-fluoro-benzylamino)-imidazo[1,2-a]pyridine-6-carboxamide mesylate

HRID 427490

Reaktionsgleichung

Reaktionsgleichung von HRID 427490
[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.[CH3:21][C:22]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([CH3:31])[C:23]=1[CH2:24]Br.C(N(C(C)C)CC)(C)C.[I-].[K+]>CN(C)C=O.C(Cl)Cl.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][CH2:24][C:23]3[C:22]([CH3:21])=[CH:29][C:28]([F:30])=[CH:27][C:26]=3[CH3:31])=[CH:12][C:11]([C:13]([NH2:15])=[O:14])=[CH:10][N:9]2[C:16]=1[CH3:20]

Komponenten

8

Edukt 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 183574358-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide mesylateHCID 226726412-(Bromomethyl)-5-fluoro-1,3-dimethylbenzene

Produkt 1

HCID 183574282,3-Dimethyl-8-(2,6-dimethyl-4-fluoro-benzylamino)-imidazo[1,2-a]pyridine-6-carboxamide mesylateAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

8-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide mesylate (5.0 g, 13.4 mmol), 2,6-dimethyl-4-fluorobenzylbromide (2.91 g, 13.4 mmol), diisopropylethylamin (3.8 g, 29.5 mmol) and a cat. amount of potassium iodide were stirred in dimethylformamide (20 ml) at room temperature overnight. Water (70 ml) and methylene chloride (2×50 ml) were added to the reaction mixture and the organic layer was separated, dried and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride:methanol (9:1) as eluent. The product was solved in isopropanol and methansulfonic acid (0.3 g) was added. The salt that formed was isolated by filtration and washed with isopropanol and diethyl ether to give 1.4 g (24%) of the title compound.

Aufarbeitung

  1. customthe organic layer was separated
  2. customdried
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. additionmethansulfonic acid (0.3 g) was added
  6. customThe salt that formed
  7. customwas isolated by filtration
  8. washwashed with isopropanol and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-a4b2a0765c7648a995700ffb6597e00f
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313137B1

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