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

HRID 2300168노트

반응식

HRID 2300168 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
170 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f8b7a19dfbf04b3eb9dbf7d77971ea8e
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498159B1

반응 노트

불러오는 중…