Water → 8-(cyclohexylmethoxy)-2-methyl-N-[(1R)-2-(methylamino)-1-phenylethyl]imidazo[1,2-a]pyridine-3-carboxamide

HRID 64483

반응식

HRID 64483 반응식
[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][C@H:22]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH2:23][N:24]([CH3:37])S(C4C=CC=CC=4[N+]([O-])=O)(=O)=O)=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S)=CC=1.O>CN(C=O)C.C(Cl)(Cl)Cl.CO>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][C@H:22]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH2:23][NH:24][CH3:37])=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 962WaterHCID 78114-MethylbenzenethiolHCID 11430Potassium CarbonateHCID 867135138-(cyclohexylmethoxy)-2-methyl-N-[(1R)-2-{methyl[(2-nitrophenyl)sulfonyl]amino}-1-phenylethyl]imidazo[1,2-a]pyridine-3-carboxamide

생성물 1

HCID 867135128-(cyclohexylmethoxy)-2-methyl-N-[(1R)-2-(methylamino)-1-phenylethyl]imidazo[1,2-a]pyridine-3-carboxamide수율 57.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21584188Chloroform methanol용매

실험 절차

To a solution of 200 mg of 8-(cyclohexylmethoxy)-2-methyl-N-[(1R)-2-{methyl[(2-nitrophenyl)sulfonyl]amino}-1-phenylethyl]imidazo[1,2-a]pyridine-3-carboxamide in 3 ml of DMF were added 140 mg of potassium carbonate and 50 mg of 4-methylbenzenethiol, followed by stirring for 3 hours. To the reaction mixture were added water and chloroform/methanol (9/1) 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 80 mg of 8-(cyclohexylmethoxy)-2-methyl-N-[(1R)-2-(methylamino)-1-phenylethyl]imidazo[1,2-a]pyridine-3-carboxamide.

후처리

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

출처 및 근거

ORD 기록
ord-d71a4acd9ada45b696e2cdde6d35b19c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447090B2

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