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

HRID 427490Notes

Reaction equation

HRID 427490 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.[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a4b2a0765c7648a995700ffb6597e00f
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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