Dichloromethane → Methyl 4-[({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)methyl]-1-(methylsulfonyl)piperidine-4-carboxylate

HRID 64466노트

반응식

HRID 64466 반응식
Cl.Cl.[CH:3]1([CH2:9][O:10][C:11]2[C:12]3[N:13]([C:17]([C:21]([NH:23][CH2:24][C:25]4([C:31]([O:33][CH3:34])=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[O:22])=[C:18]([CH3:20])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C(N(CC)CC)C.ClCCl.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>C(OCC)(=O)C.O>[CH:3]1([CH2:9][O:10][C:11]2[C:12]3[N:13]([C:17]([C:21]([NH:23][CH2:24][C:25]4([C:31]([O:33][CH3:34])=[O:32])[CH2:30][CH2:29][N:28]([S:46]([CH3:45])(=[O:48])=[O:47])[CH2:27][CH2:26]4)=[O:22])=[C:18]([CH3:20])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86713485Methyl 4-[({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)methyl]piperidine-4-carboxylate dihydrochloride

생성물 1

HCID 86713487Methyl 4-[({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)methyl]-1-(methylsulfonyl)piperidine-4-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 150 mg of methyl 4-[({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)methyl]piperidine-4-carboxylate dihydrochloride, 150 μl of triethylamine, and 5 ml of dichloromethane was added 35 μl of methanesulfonyl chloride under ice-cooling, followed by stirring at room temperature for 2 hours. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 85 mg of methyl 4-[({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)methyl]-1-(methylsulfonyl)piperidine-4-carboxylate.

후처리

  1. temperaturecooling
  2. customa layer separation operation
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ac80e16aecd8435586390a6e67618cd6
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447090B2

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