Tetrahydrofuran → 2-(3-[3-Methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[3-(trifluoromethyl)phenoxy]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}propan-2-ol

HRID 71161노트

반응식

HRID 71161 반응식
[CH3:1][Mg]Br.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:18]2[N:22]3[CH2:23][CH2:24][CH2:25][C:26]([O:32][C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=4)(C(OCC)=O)[C:21]3=[N:20][N:19]=2)[CH:9]=[CH:10][C:11]=1[C:12]1[O:16][C:15]([CH3:17])=N[CH:13]=1.[Cl-].[NH4+:44].[CH2:45]1[CH2:49][O:48]CC1>>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:18]2[N:22]3[CH2:23][CH2:24][CH2:25][C:26]([C:49]([OH:48])([CH3:45])[CH3:1])([O:32][C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:40])([F:42])[F:41])[CH:34]=4)[C:21]3=[N:20][N:19]=2)[CH:9]=[CH:10][C:11]=1[C:12]1[O:16][C:15]([CH3:17])=[N:44][CH:13]=1

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 66608183Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[3-(trifluoromethyl)phenoxy]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylateHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 569295452-(3-[3-Methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[3-(trifluoromethyl)phenoxy]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}propan-2-ol

실험 절차

Methylmagnesium bromide (1 M THF solution, 5.81 mL) was added to a mixture of ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[3-(trifluoromethyl)phenoxy]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (630 mg) in THF (7 mL) under ice-cooling, and the mixture was stirred for 1 hr. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (270 mg).

후처리

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-b282179d69e24554ba5b7b2011a511f3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822699B2

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