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

HRID 2401218ノート

反応式

HRID 2401218 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]([F:26])([F:25])[F:24])[N:20]=[CH:19][N:18]=1.CCN(C(C)C)C(C)C>CN1CCCC1=O.C(OCC)(=O)C.C(#N)C.CS(C)=O>[F:24][C:23]([F:26])([F:25])[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

参加物

8

反応物 3

HCID 81531DiisopropylethylamineHCID 115428814-Chloro-6-(trifluoromethyl)pyrimidineHCID 671114591H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)-2 回

生成物 1

HCID 510499946-(Trifluoromethyl)-N-{[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}-4-pyrimidinamine収率 33%

試薬・触媒・溶媒 4

HCID 679Dimethyl Sulfoxide溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

1-[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 130 mg, 0.604 mmol), 4-chloro-6-(trifluoromethyl)pyrimidine (165 mg, 0.906 mmol) and DIPEA (0.211 mL, 1.208 mmol) in N-methyl-2-pyrrolidone (2 mL) were stirred at 150° C. for 1 hour in the microwave. The reaction mixture was diluted with ethyl acetate (25 mL) and washed with water (10 mL), brine (10 mL), water (10 mL) and brine (10 mL). The organic layer was dried (sodium sulfate), filtered and concentrated under reduced pressure to give a brown oil. This oil was dissolved in a mixture of acetonitrile and DMSO (1:1) (2.7 mL) and purified by MDAP (3 injections). Fractions containing the suspected product were combined and concentrated under reduced pressure to give the title compound as a pale brown solid (72 mg);

後処理

  1. washwashed with water (10 mL), brine (10 mL), water (10 mL) and brine (10 mL)
  2. dry with materialThe organic layer was dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a brown oil
  6. custompurified by MDAP (3 injections)
  7. additionFractions containing the suspected product
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-731242e8fd914d4cb5d14be2b8b1104b
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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