Sodium ethoxide → Ethyl 8-[6-(2-ethoxy-2-oxoethyl)-2,3,4-trifluorophenoxy]-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 1398246노트

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HRID 1398246 반응식
[F:1][C:2]1[C:3]([OH:16])=[C:4]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[O-]CC.[Na+].Cl[C:22]1([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:27][CH2:26][CH2:25][N:24]2[C:28]([C:31]3[CH:36]=[CH:35][C:34]([C:37]4[O:41][C:40]([CH3:42])=[N:39][CH:38]=4)=[C:33]([O:43][CH3:44])[CH:32]=3)=[N:29][N:30]=[C:23]12>C(O)C.[Cl-].[NH4+]>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][C:4]1[C:3]([O:16][C:22]2([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:27][CH2:26][CH2:25][N:24]3[C:28]([C:31]4[CH:36]=[CH:35][C:34]([C:37]5[O:41][C:40]([CH3:42])=[N:39][CH:38]=5)=[C:33]([O:43][CH3:44])[CH:32]=4)=[N:29][N:30]=[C:23]23)=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=1)[CH3:15]

참가 물질

6

반응물 3

HCID 2723922Sodium ethoxideHCID 66604255Ethyl 8-chloro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylateHCID 86662985Ethyl (3,4,5-trifluoro-2-hydroxyphenyl)acetate

생성물 1

HCID 86662984Ethyl 8-[6-(2-ethoxy-2-oxoethyl)-2,3,4-trifluorophenoxy]-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate수율 45.2%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 25517Ammonium Chloride용매

실험 절차

To a mixture of ethyl (3,4,5-trifluoro-2-hydroxyphenyl)acetate (1.77 g) in ethanol (15 mL) was added sodium ethoxide (0.514 g) at room temperature under a nitrogen atmosphere, and the mixture was stirred for 30 min. To the reaction mixture was added ethyl 8-chloro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (3 g), the mixture was stirred at 80° C. overnight under a nitrogen atmosphere, and diluted with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2 g).

후처리

  1. stirringthe mixture was stirred at 80° C. overnight under a nitrogen atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-f0af5ac1d0ac47439fefc0a62a88f690
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901309B2

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