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4-Methylmorpholine → 8-[(2-fluorobenzyl)oxy]-6-(hydroxymethyl)-N-[(1R)-2-hydroxy-1-phenylethyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide

HRID 64473
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HRID 64473 반응식
[F:1][C:2]1[CH:34]=[CH:33][CH:32]=[CH:31][C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:15]([C:19](=[O:30])[NH:20][C@H:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:22][OH:23])=[C:16]([CH3:18])[N:17]=2)[CH:9]=[C:10]([C:12](O)=[O:13])[CH:11]=1.CN1CCOCC1.ClC(OCC(C)C)=O>C(COC)OC>[F:1][C:2]1[CH:34]=[CH:33][CH:32]=[CH:31][C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:15]([C:19]([NH:20][C@H:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:22][OH:23])=[O:30])=[C:16]([CH3:18])[N:17]=2)[CH:9]=[C:10]([CH2:12][OH:13])[CH:11]=1
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참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 867135018-[(2-fluorobenzyl)oxy]-3-{[(1R)-2-hydroxy-1-phenylethyl]carbamoyl}-2-methylimidazo[1,2-a]pyridine-6-carboxylic acid

생성물 1

HCID 867135008-[(2-fluorobenzyl)oxy]-6-(hydroxymethyl)-N-[(1R)-2-hydroxy-1-phenylethyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide수율 21.7%

시약·촉매·용매 1

HCID 8071
1,2-Dimethoxyethane
용매

실험 절차

To a mixture of 100 mg of 8-[(2-fluorobenzyl)oxy]-3-{[(1R)-2-hydroxy-1-phenylethyl]carbamoyl}-2-methylimidazo[1,2-a]pyridine-6-carboxylic acid, 28 μl of 4-methylmorpholine, and 0.7 ml of dimethoxyethane was added 34 μl of isobutyl chloroformate under ice-cooling, followed by stirring at room temperature overnight. The insoluble material was removed by filtration, and then to the filtrate were added 16 mg of sodium borohydride and 210 μl of methanol under ice-cooling, followed by stirring for 30 minutes under ice-cooling. To the reaction mixture were added a saturated aqueous ammonium chloride solution and chloroform to carry out a layer separation operation. The organic layer was 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 21 mg of 8-[(2-fluorobenzyl)oxy]-6-(hydroxymethyl)-N-[(1R)-2-hydroxy-1-phenylethyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

후처리

  1. temperaturecooling
  2. customThe insoluble material was removed by filtration
  3. additionto the filtrate were added 16 mg of sodium borohydride and 210 μl of methanol under ice-
  4. temperaturecooling
  5. stirringby stirring for 30 minutes under ice-
  6. temperaturecooling
  7. additionTo the reaction mixture were added a saturated aqueous ammonium chloride solution and chloroform
  8. customa layer separation operation
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-69b27d3efd244c969e16e6c8e4869c4f
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09447090B2

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