Dimethylformamide → 2,3-Dimethyl-8-(2-bromo-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide

HRID 427494노트

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HRID 427494 반응식
S(O)(=O)(=O)C.[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.[Br:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:23]=1[CH2:24]Cl.C(N(C(C)C)CC)(C)C.CN(C)C=O>O.C(Cl)Cl>[CH3:19][C:17]1[N:18]=[C:8]2[C:7]([NH:6][CH2:24][C:23]3[C:26]([CH3:30])=[CH:27][CH:28]=[CH:29][C:22]=3[Br:21])=[CH:12][C:11]([C:13]([NH2:15])=[O:14])=[CH:10][N:9]2[C:16]=1[CH3:20]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 183574341-Bromo-2-(chloromethyl)-3-methylbenzeneHCID 183574358-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide mesylate

생성물 1

HCID 98650172,3-Dimethyl-8-(2-bromo-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide수율 9.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

8-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide mesylate (1.0 g, 5.0 mmol), 2-bromo-6-methylbenzylchloride (45%)(3.0 g, 5.0 mmol) and diisopropylethylamin (2.2 g, 17 mmol) were added to dimethylformamide (50 ml) and stirred at 50° C. for 48 h. Methylene chloride and water were added to the reaction mixture, the organic layer was separated, washed with saturated sodium chloride, dried (Na2SO4) and evaporated under reduced pressure. Purification of the residue twice by column chromatography on silica gel using methylene chloride:methanol (10:1) and ethylacetate as eluent gave 0.18 g (1%) of the desired product.

후처리

  1. customthe organic layer was separated
  2. washwashed with saturated sodium chloride
  3. dry with materialdried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customPurification of the residue twice by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-2e3679b0ebe64071937205063e296722
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313137B1

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