Diisopropylethylamine → 3-(2-Ethoxypyridin-3-yl)-3-[4-(4-methylpiperazin-1-ylmethyl)phenylamino]-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile

HRID 469200

반응식

HRID 469200 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.Cl[C:17]1([C:29]2[C:30]([O:35][CH2:36][CH3:37])=[N:31][CH:32]=[CH:33][CH:34]=2)[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[N:27])[CH:24]=2)[NH:19][C:18]1=[O:28].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>ClCCl>[CH2:36]([O:35][C:30]1[C:29]([C:17]2([NH:15][C:12]3[CH:13]=[CH:14][C:9]([CH2:8][N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:10][CH:11]=3)[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[N:27])[CH:24]=3)[NH:19][C:18]2=[O:28])=[CH:34][CH:33]=[CH:32][N:31]=1)[CH3:37]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 670485043-Chloro-3-(2-ethoxypyridin-3-yl)-2-oxoindoline-5-carbonitrile

생성물 1

HCID 671980643-(2-Ethoxypyridin-3-yl)-3-[4-(4-methylpiperazin-1-ylmethyl)phenylamino]-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile수율 103.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-(4-Methyl-piperazin-1-ylmethyl)phenylamine (425 mg, 2.07 mmol) was added to a solution of 3-chloro-3-(2-ethoxypyridin-3-yl)-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile (500 mg, 1.59 mmol) in dichloromethane (50 ml) and DIPEA (0.27 ml, 159 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 h and then an aqueous NaHCO3 solution was added. The aqueous reaction mixture was extracted with dichloromethane. The combined organic phase was dried over magnesium sulfate, filtered and concentrated at reduced pressure. Purification by chromatography (silica gel, 0-20% methanol in dichloromethane) afforded 791 mg of the title compound (99% yield).

후처리

  1. extractionThe aqueous reaction mixture was extracted with dichloromethane
  2. dry with materialThe combined organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. customPurification by chromatography (silica gel, 0-20% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-2bd343301a104a76b3c1f9c82d82b970
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629148B2

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