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

HRID 17473ノート

反応式

HRID 17473 の反応式
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.F[C:17]1[C:18]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:19]([CH3:34])[C:20]([C:32]#[N:33])=[C:21]2[C:25]=1[O:24][C:23]([C:26]1[CH:31]=[N:30][CH:29]=[CH:28][N:27]=1)=[N:22]2>CS(C)=O>[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][N:5]([C:17]2[C:18]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:19]([CH3:34])[C:20]([C:32]#[N:33])=[C:21]3[C:25]=2[O:24][C:23]([C:26]2[CH:31]=[N:30][CH:29]=[CH:28][N:27]=2)=[N:22]3)[CH2:4]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685858077-Fluoro-5-methyl-6-phenyl-2-(pyrazin-2-yl)-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 685848897-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-(pyrazin-2-yl)-1,3-benzoxazole-4-carbonitrile収率 38.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
95 °C

実験手順

(3S)-3-(Dimethylamino)pyrrolidine (93.4 μl, 0.736 mmol) and triethylamine (121 μl, 0.866 mmol) were added to a dimethyl sulfoxide (4 ml) solution of 7-fluoro-5-methyl-6-phenyl-2-(pyrazin-2-yl)-1,3-benzoxazole-4-carbonitrile (I-187) (143 mg, 0.433 mmol), followed by stirring in an oil bath at 95° C. for 0.2 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in chloroform (100 ml), washed with saturated brine (50 ml). After drying over anhydrous sodium sulfate, the solvent was evaporated away, and the resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=9:1), the eluate was recrystallized from isopropanol to obtain the entitled compound (71.0 mg, 38.6%) as a pale yellow acicular crystal.

後処理

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform (100 ml)
  4. washwashed with saturated brine (50 ml)
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated away
  7. customthe resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=9:1)
  8. customthe eluate was recrystallized from isopropanol

出典と根拠

ORDレコード
ord-3c628e19145d41678b001e2745aa5a87
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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