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

HRID 2401220ノート

反応式

HRID 2401220 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[N:22]=[CH:21][N:20]=[C:19]([C:23]#[N:24])[CH:18]=1.CCN(C(C)C)C(C)C>CN1CCCC1=O.C(OCC)(=O)C>[F:15][C:2]([F:1])([F:14])[C:3]1[NH:13][C:6]2=[N:7][CH:8]=[C:9]([CH2:11][NH:12][C:17]3[N:22]=[CH:21][N:20]=[C:19]([C:23]#[N:24])[CH:18]=3)[CH:10]=[C:5]2[CH:4]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 224988816-Chloropyrimidine-4-carbonitrile2 回HCID 671114591H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)-2 回

生成物 1

HCID 513558706-({[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}amino)-4-pyrimidinecarbonitrile収率 21.6%

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
100 °C

実験手順

1-[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 100 mg, 0.465 mmol), 6-chloro-4-pyrimidinecarbonitrile (Intermediate 8, 97 mg, 0.697 mmol) and DIPEA (0.162 mL, 0.929 mmol) were added together in N-methyl-2-pyrrolidone (2 mL) and the resulting mixture was heated at 100° 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 an off-white solid (32 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-0ce8d75243884b3893e832a498091fe2
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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