Ammonium Chloride → 6-(2,4-Difluorophenoxy)-1-(2-trimethylsilanyl-ethoxymethyl)-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one

HRID 230175노트

반응식

HRID 230175 반응식
C[O:2][C:3](=O)[CH:4]([O:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[F:31])[CH:5](O)[C:6]1[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:8]=[CH:9][C:10]=1[N+:11]([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[O:23][C:4]1[C:3](=[O:2])[NH:11][C:10]2[CH:9]=[N:8][N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=2[CH:5]=1

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 598129592-(2,4-difluorophenoxy)-3-hydroxy-3-[4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]propionic acid methyl ester

생성물 1

HCID 598129756-(2,4-Difluorophenoxy)-1-(2-trimethylsilanyl-ethoxymethyl)-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one수율 94.3%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

To a solution of 2-(2,4-difluorophenoxy)-3-hydroxy-3-[4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]propionic acid methyl ester (125 mg, 0.264 mmol) in ethanol (2 mL) and water (1 mL) was added ammonium chloride (74 mg, 5.2 eq) followed by iron powder (Fisher Brand, Electrolytic). The resulting mixture was stirred at room temperature for 45 minutes, refluxed overnight, cooled to room temperature, diluted with ethanol, and filtered through a 3 cm bed of celite with additional ethanol. The filtrate was concentrated, and the residue was diluted with ethyl acetate (80 mL) and water (40 mL). The organic layer was separated, washed with water (2×40 mL) and brine (1×40 mL), dried over magnesium sulfate, filtered and concentrated to give the title compound as a thick tan oil (98 mg, (M+H)+=394).

후처리

  1. temperaturerefluxed overnight
  2. temperaturecooled to room temperature
  3. filtrationfiltered through a 3 cm bed of celite with additional ethanol
  4. concentrationThe filtrate was concentrated
  5. additionthe residue was diluted with ethyl acetate (80 mL) and water (40 mL)
  6. customThe organic layer was separated
  7. washwashed with water (2×40 mL) and brine (1×40 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-df5008a60bd044d9b4b22e384df36df1
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566708B2

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