Triethylamine → HCID 68585189、化合物

HRID 17477ノート

反応式

HRID 17477 の反応式
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[CH2:9](N(CC)CC)C.F[C:17]1[C:18]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[C:19]([CH3:36])[C:20]([C:34]#[N:35])=[C:21]2[C:25]=1[O:24][C:23]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)(C)[NH: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:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:19]([CH3:36])[C:20]([C:34]#[N:35])=[C:21]3[C:25]=2[O:24][C:23]([N:27]([CH3:9])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[N:22]3)[CH2:4]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685847727-Fluoro-5-methyl-2-methylpyridin-2-ylamino-6-phenyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 68585189HCID 68585189、化合物収率 26.4%

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 (63.2 μl, 0.498 mmol) and triethylamine (81.7 μl, 0.586 mmol) were added to a dimethyl sulfoxide (3 ml) solution of 7-fluoro-5-methyl-2-methylpyridin-2-ylamino-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-189) (105 mg, 0.293 mmol), followed by stirring in an oil bath at 95° C. for 2 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in chloroform (50 ml), washed with saturated brine (50 ml). After drying over anhydrous sodium sulfate and concentration, the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=20:1), and the obtained eluate was recrystallized from isopropanol to obtain the entitled compound (35.0 mg, 26.4%) as a colorless solid.

後処理

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform (50 ml)
  4. washwashed with saturated brine (50 ml)
  5. dry with materialAfter drying over anhydrous sodium sulfate and concentration
  6. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=20:1)
  7. customthe obtained eluate was recrystallized from isopropanol

出典と根拠

ORDレコード
ord-f9b627c6ef7c4f7dad3ebeb10f0f4ec0
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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