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

反応式

HRID 17318 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4bf106d9387a4d12a650fb0b39fbb4e9
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

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