Potassium Carbonate → 4-amino-5-chloro-N-(1-(5-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)pentyl)piperidin-4-ylmethyl)-2-methoxybenzamide

HRID 344381

반응식

HRID 344381 반응식
Cl.[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:8])=[C:5]([O:20][CH3:21])[CH:4]=1.[C:22](=[O:25])([O-])[O-].[K+].[K+].BrCCCCC[C:34]1[CH:44]=[CH:43][CH:42]=[C:36]2[C:37]([NH:39][C:40](=[O:41])[C:35]=12)=O>CN(C)C=O>[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:18][CH2:3][CH2:4][CH2:5][CH2:37][N:39]3[C:40](=[O:41])[C:35]4[C:34](=[CH:44][CH:43]=[CH:42][CH:36]=4)[C:22]3=[O:25])[CH2:15][CH2:16]2)=[O:8])=[C:5]([O:20][CH3:21])[CH:4]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 22352176HCID 22352176, 화합물HCID 667809414-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride

생성물 1

HCID 543795694-amino-5-chloro-N-(1-(5-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)pentyl)piperidin-4-ylmethyl)-2-methoxybenzamide수율 113.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride (23.0 g) was dissolved in dimethylformamide (250 ml). Potassium carbonate (28.5 g) and 5-bromopentylphthalimide (20.4 g) were added, and the mixture was stirred at 50° C. for 8 hr. The reaction mixture was concentrated under reduced pressure and the residue was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to give 20.0 g of 4-amino-5-chloro-N-(1-(5-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)pentyl)piperidin-4-ylmethyl)-2-methoxybenzamide.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-dfee23cb27344e6f8d8bc7c79bc37237
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05864039

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