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

HRID 427490ノート

反応式

HRID 427490 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a4b2a0765c7648a995700ffb6597e00f
出典データセット
uspto-grants-2001_11
特許番号
US06313137B1

反応ノート

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