Dimethyl Sulfoxide → 2-[2-(Benzyloxy)-1,1-dimethylethyl]-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17318

반응식

HRID 17318 반응식
C(N(CC)CC)C.[CH3:8][N:9]([CH3:15])[C@H:10]1[CH2:14][CH2:13][NH:12][CH2:11]1.CS(C)=O.[CH2:20]([O:27][CH2:28][C:29]([C:32]1[O:33][C:34]2[C:35](=[C:37]([C:49]#[N:50])[C:38]([CH3:48])=[C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:40]=2F)[N:36]=1)([CH3:31])[CH3:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)(=O)C>[CH2:20]([O:27][CH2:28][C:29]([C:32]1[O:33][C:34]2[C:35](=[C:37]([C:49]#[N:50])[C:38]([CH3:48])=[C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:40]=2[N:12]2[CH2:13][CH2:14][C@H:10]([N:9]([CH3:15])[CH3:8])[CH2:11]2)[N:36]=1)([CH3:31])[CH3:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685844612-(2-Benzyloxy-1,1-dimethylethyl)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

생성물 1

HCID 685860062-[2-(Benzyloxy)-1,1-dimethylethyl]-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile수율 91.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

Triethylamine (222 μl, 1.59 mmol), (3S)-3-(dimethylamino)pyrrolidine (152 μl, 1.19 mmol) were added to a dimethyl sulfoxide (16.5 ml) solution of 2-[2-(benzyloxy)-1,1-dimethylethyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-66) (330 mg, 0.796 mmol), followed by stirring overnight at 90° C. After cooling, the reaction liquid was diluted with ethyl acetate, washed three times with saturated brine, then dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to obtain the entitled compound (369 mg, 91%) as a pale brown oil.

후처리

  1. temperatureAfter cooling
  2. customthe reaction liquid
  3. washwashed three times with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1)

출처 및 근거

ORD 기록
ord-4bf106d9387a4d12a650fb0b39fbb4e9
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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