(3S)-(-)-3-(Dimethylamino)pyrrolidine → 7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17314

반응식

HRID 17314 반응식
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.F[C:10]1[C:11]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:12]([CH3:24])[C:13]([C:22]#[N:23])=[C:14]2[C:18]=1[O:17][C:16]([CH2:19][O:20][CH3:21])=[N:15]2.O.C(=O)(O)[O-].[Na+]>CS(C)=O>[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][N:5]([C:10]2[C:11]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:12]([CH3:24])[C:13]([C:22]#[N:23])=[C:14]3[C:18]=2[O:17][C:16]([CH2:19][O:20][CH3:21])=[N:15]3)[CH2:4]1

참가 물질

5

반응물 3

HCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685851157-Fluoro-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileHCID 86585896Sodium bicarbonate water

생성물 1

HCID 685844727-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile수율 17%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
90 °C

실험 절차

(3S)-3-(Dimethylamino)pyrrolidine (76 μl, 0.60 mmol) was added to a dimethyl sulfoxide (4 ml) solution of 7-fluoro-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-59) (58 mg, 0.20 mmol), followed by stirring at 90° C. for 1 hour. After cooling to room temperature, the above brown oily substance and saturated sodium bicarbonate water were added, followed by extraction three times with ethyl acetate, the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with chloroform:methanol (50:1) was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, washed twice with saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration tinder reduced pressure, the entitled compound (39 mg, 17%) was obtained as a brown oily substance.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionfollowed by extraction three times with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration and concentration under reduced pressure
  6. concentrationthe eluate with chloroform:methanol (50:1) was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washwashed twice with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationAfter filtration and concentration tinder reduced pressure

출처 및 근거

ORD 기록
ord-b341d755573047dcac0d67357cf083fb
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

연결된 노트

불러오는 중…