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

HRID 427488Notes

Reaction equation

HRID 427488 reaction equation
[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]

Participants

11

Reactant 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

Product 1

HCID 183574452,3-Dimethyl-8-(2-ethyl-4-fluoro-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide mesylateYield 23.4%

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-22b242024f4a445bbb8580cd55db0e91
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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