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

HRID 427490노트

반응식

HRID 427490 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a4b2a0765c7648a995700ffb6597e00f
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313137B1

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