Ammonia → 1-(3-Amino-3-methyl-1-butynyl)-4-[(3-chloro-4-methoxybenzyl)amino]-6-phthalazinecarbonitrile hydrochloride

HRID 47347

반응식

HRID 47347 반응식
C(N(CC)CC)C.[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]#[N:20])=[CH:16][CH:17]=2)[C:12]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([Cl:31])[CH:24]=2)=[N:11][N:10]=1.[NH2:32][C:33]([CH3:37])([CH3:36])[C:34]#[CH:35].N>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(OCC)(=O)C.CN(C)C=O>[ClH:8].[NH2:32][C:33]([CH3:37])([CH3:36])[C:34]#[C:35][C:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]#[N:20])=[CH:16][CH:17]=2)[C:12]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([Cl:31])[CH:24]=2)=[N:11][N:10]=1

참가 물질

9

반응물 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 763193-Butyn-2-amine, 2-methyl-HCID 104510651-Chloro-4-((3-chloro-4-methoxybenzyl)amino)-6-phthalazinecarbonitrile

생성물 1

HCID 227444991-(3-Amino-3-methyl-1-butynyl)-4-[(3-chloro-4-methoxybenzyl)amino]-6-phthalazinecarbonitrile hydrochloride수율 72.4%

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

0.39 ml triethylamine was added to a mixture of 500 mg 1-chloro-4-[(3-chloro-4-methoxybenzyl)amino]-6-phthalazine carbonitrile, 53 mg cuprous iodide, 98 mg dichlorobis(triphenylphosphine)palladium (II), 347 mg 3-amino-3-methyl-1-butyne, and 10 ml dimethylformamide, and the mixture was stirred at 80° C. for 3 hr in a nitrogen atmosphere. After cooling, ethyl acetate was added to the reaction solution, then water and conc. aqueous ammonia were added thereto, and the organic layer was recovered. The organic layer was washed with dilute aqueous ammonia and brine, and dried over anhydrous sodium sulfate. It was filtered and the filtrate was evaporated. The resulting residue was purified by NH-form silica gel column chromatography to give 446 mg of the title compound. The product was converted in a usual manner into the hydrochloride.

후처리

  1. temperatureAfter cooling
  2. customthe organic layer was recovered
  3. washThe organic layer was washed with dilute aqueous ammonia and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationIt was filtered
  6. customthe filtrate was evaporated
  7. customThe resulting residue was purified by NH-form silica gel column chromatography

출처 및 근거

ORD 기록
ord-2d8b3da9fef948209fab9deea4af6ff3
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699870B2

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