N-methyl-2-pyrrolidone → 4-(3-Chloro-4-methoxybenzyl)amino-6-cyano-1-(4-cyanopiperidino)phthalazine hydrochloride

HRID 47332ノート

反応式

HRID 47332 の反応式
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]#[N:9])[CH2:4][CH2:3]1.[Cl:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]#[N:22])=[CH:18][CH:19]=2)[C:14]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([Cl:33])[CH:26]=2)=[N:13][N:12]=1.C(N(C(C)C)CC)(C)C.CN1CCCC1=O>C(OCC)(=O)C>[ClH:10].[Cl:33][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[O:31][CH3:32])[CH2:24][NH:23][C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=2)[C:11]([N:2]2[CH2:7][CH2:6][CH:5]([C:8]#[N:9])[CH2:4][CH2:3]2)=[N:12][N:13]=1

参加物

6

反応物 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 104510651-Chloro-4-((3-chloro-4-methoxybenzyl)amino)-6-phthalazinecarbonitrileHCID 227446374-Piperidinecarbonitrile hydrochloride

生成物 1

HCID 227445544-(3-Chloro-4-methoxybenzyl)amino-6-cyano-1-(4-cyanopiperidino)phthalazine hydrochloride収率 67.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
170 °C

実験手順

A mixture of 1.2 g of the resulting 4-piperidinecarbonitrile hydrochloride, 1.0 g 1-chloro-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine, 1.8 g diisopropylethylamine, and 10 ml 1-methyl-2-pyrrolidone was stirred at 170° C. for 2 hr and 30 min. After cooling, ethyl acetate was added to the reaction solution which was then washed with water and brine. After it was dried over anhydrous sodium sulfate, the solvent was evaporated and the resulting residue was purified by silica gel column chromatography. The resulting free compound was dissolved in ethyl acetate, then a solution of 4 N hydrochloric acid/ethyl acetate was added thereto, and the resulting crystals were collected by filtration to give 880 mg of the title compound as a yellow powder.

後処理

  1. temperatureAfter cooling
  2. washwas then washed with water and brine
  3. dry with materialAfter it was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography
  6. dissolutionThe resulting free compound was dissolved in ethyl acetate
  7. additiona solution of 4 N hydrochloric acid/ethyl acetate was added
  8. filtrationthe resulting crystals were collected by filtration

出典と根拠

ORDレコード
ord-7679366578cc4903857d63e6485b8519
出典データセット
uspto-grants-2004_03
特許番号
US06699870B2

反応ノート

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