Potassium Carbonate → 5-(Benzoxazol-2-yl)-2-methyl-1-(3-phenylpropyl)benzimidazole

HRID 74231

반응식

HRID 74231 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-])=O.C(=O)([O-])[O-].[K+].[K+].[C:26]1([CH2:32][CH2:33][CH2:34][NH2:35])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[H][H].CO[C:40](OC)(OC)[CH3:41]>C(O)C.CO.[C].[Pd].O>[O:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]2[N:35]([CH2:34][CH2:33][CH2:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:40]([CH3:41])=[N:17][C:3]=2[CH:4]=1

참가 물질

10

반응물 5

HCID 11430Potassium CarbonateHCID 15050Trimethyl orthoacetateHCID 162593-PhenylpropylamineHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 674980645-(Benzoxazol-2-yl)-2-methyl-1-(3-phenylpropyl)benzimidazole수율 17.8%

시약·촉매·용매 4

HCID 178418390HCID 178418390, 화합물촉매HCID 702Ethanol용매HCID 887Methanol용매HCID 962Water용매

실험 절차

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.16 mmol) in ethanol (5 mL) was added potassium carbonate (176 mg, 1.28 mmol) and 3-phenylpropylamine (189 mg, 1.39 mmol), and this was heated to reflux for 3 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a tetrahydrofuran solution (5 mL) of the crystals obtained was added 10% palladium-carbon (50 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 6 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was dissolved in methanol (5 mL), and to this was added 1,1,1-trimethoxyethane (108 mg, 0.896 mmol), and this was heated to reflux for 6 hours. After the reaction was complete, this was concentrated, and the residue obtained was purified by silica gel column chromatography to yield the title compound (58.5 mg, 14% yield) as white crystals.

후처리

  1. temperaturethis was heated
  2. temperatureto reflux for 3 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a tetrahydrofuran solution (5 mL) of the crystals obtained
  7. filtrationthis was filtered through Celite
  8. concentrationthe filtrate was concentrated
  9. customThe residue obtained
  10. temperaturethis was heated
  11. temperatureto reflux for 6 hours
  12. concentrationthis was concentrated
  13. customthe residue obtained
  14. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-195f30aa87854e2c8186d29248fe96ca
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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