Diisopropylethylamine → 6-(1,1-Dimethylethyl)-N-{[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}-4-pyrimidinamine

HRID 2401221ノート

反応式

HRID 2401221 の反応式
[F:1][C:2]([F:15])([F:14])[C:3]1[NH:13][C:6]2=[N:7][CH:8]=[C:9]([CH2:11][NH2:12])[CH:10]=[C:5]2[CH:4]=1.Cl[C:17]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:20]=[CH:19][N:18]=1.CCN(C(C)C)C(C)C>CN1CCCC1=O.C(OCC)(=O)C>[CH3:24][C:23]([C:21]1[N:20]=[CH:19][N:18]=[C:17]([NH:12][CH2:11][C:9]2[CH:10]=[C:5]3[CH:4]=[C:3]([C:2]([F:1])([F:14])[F:15])[NH:13][C:6]3=[N:7][CH:8]=2)[CH:22]=1)([CH3:26])[CH3:25]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 42892434-Chloro-6-(1,1-dimethylethyl)pyrimidine2 回HCID 671114591H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)-2 回

生成物 1

HCID 513558716-(1,1-Dimethylethyl)-N-{[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}-4-pyrimidinamine収率 13.9%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

1-[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 75 mg, 0.349 mmol), 4-chloro-6-(1,1-dimethylethyl)pyrimidine (Intermediate 10, 89 mg, 0.523 mmol) and DIPEA (0.122 mL, 0.697 mmol) were added together in N-methyl-2-pyrrolidone (2 mL) and the resulting mixture was heated at 120° C. for 2 hours and allowed to cool to room temperature. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was separated, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by MDAP. Product containing fractions were combined and evaporated under reduced pressure. The resulting solid was dried under high vacuum at 45° C. for 18 hours to give the title compound as a white solid (17 mg);

後処理

  1. temperatureto cool to room temperature
  2. washwashed with water and brine
  3. customThe organic layer was separated
  4. customdried under magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by MDAP
  7. additionProduct containing fractions
  8. customevaporated under reduced pressure
  9. customThe resulting solid was dried under high vacuum at 45° C. for 18 hours

出典と根拠

ORDレコード
ord-f723faa7b6244bac9c5f292e8fbbbd03
出典データセット
uspto-grants-2014_08
特許番号
US08796283B2

反応ノート

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