Sodium Carbonate → 4-[(3-Chloro-4-methoxybenzyl)amino]-1-[4-(methoxyimino)piperidino]-6-phthalazine carbonitrile

HRID 2300184노트

반응식

HRID 2300184 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[C:10]([N:19]2[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]2)=[N:9][N:8]=1.Cl.[CH3:32][O:33][NH2:34].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[C:10]([N:19]2[CH2:20][CH2:21][C:22](=[N:34][O:33][CH3:32])[CH2:23][CH2:24]2)=[N:9][N:8]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 105040684-(3-Chloro-4-methoxy-benzylamino)-1-(4-oxo-piperidin-1-yl)-phthalazine-6-carbonitrile; hydrochloride

생성물 1

HCID 227444584-[(3-Chloro-4-methoxybenzyl)amino]-1-[4-(methoxyimino)piperidino]-6-phthalazine carbonitrile수율 48.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 1.19 g 4-[(3-chloro-4-methoxybenzyl)amino]-1-[4-oxopiperidino]-6-phthalazine carbonitrile, 354 mg methoxyamine hydrochloride, 1.2 g sodium carbonate, and 10 ml ethanol was heated under reflux for 2 hr. After cooling, saline was added to the reaction solution which was then extracted with ethyl acetate. It was dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated, and the resulting residue was purified by silica gel column chromatography to give 620 mg of 4-[(3-chloro-4-methoxybenzyl)amino]-1-[4-(methoxyimino)piperidino]-6-phthalazine carbonitrile. This product was dissolved in a mixed solvent of methanol and ethanol, and recrystallized by adding 0.35 ml of 4 N hydrochloric acid/ethyl acetate to give 388 mg of 4-[(3-chloro-4-methoxybenzyl)amino]-1-[4-(methoxyimino)piperidino]-6-phthalazinecarbonitrile hydrochloride.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hr
  3. temperatureAfter cooling
  4. additionsaline was added to the reaction solution which
  5. extractionwas then extracted with ethyl acetate
  6. dry with materialIt was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated
  9. customthe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f57768c44f2a464d82eff9f11dad4796
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498159B1

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