N-Methylaniline → 4-Chloro-N,3-dimethyl-N-phenyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

HRID 497936ノート

反応式

HRID 497936 の反応式
O[C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]2[N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:12]=[C:13]([CH3:14])[C:3]=12.P(Cl)(Cl)([Cl:23])=O.[CH3:26][NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>O1CCCC1>[Cl:23][C:2]1[C:7]([C:8]([N:27]([CH3:26])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:10])=[CH:6][N:5]=[C:4]2[N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:12]=[C:13]([CH3:14])[C:3]=12

参加物

6

反応物 4

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178433901HCID 178433901、化合物

生成物 1

HCID 223202774-Chloro-N,3-dimethyl-N-phenyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide収率 76.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

A solution of 4-hydroxy-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (2.0 g, 7.4 mmol) in phosphorous oxychloride (15 mL, 63 mmol) was heated and stirred at 100° C. for 3 hours. After the solution was cooled to room temperature, the solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (50 mL). To the solution, a solution of N-methylaniline (1.0 mL, 9.2 mmol) and triethylamine (5.2 mL, 37 mmol) in tetrahydrofuran (10 mL) was added at 0° C. After the mixture was stirred at room temperature for 1.5 hours, the reaction solvent was evaporated under reduced pressure. Purification of the residue thus obtained by silica gel chromatography (chloroform:methanol=50:1 to 20:1) gave the title compound (2.14 g, 76% yield).

後処理

  1. temperatureAfter the solution was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in tetrahydrofuran (50 mL)
  4. stirringAfter the mixture was stirred at room temperature for 1.5 hours
  5. customthe reaction solvent was evaporated under reduced pressure
  6. customPurification of the residue
  7. customthus obtained by silica gel chromatography (chloroform:methanol=50:1 to 20:1)

出典と根拠

ORDレコード
ord-8754d2e208d74794a8391091af0ed37a
出典データセット
uspto-grants-2005_09
特許番号
US06949648B2

反応ノート

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