Toluene → 4-Amino-5-chloro-N-(1-(4-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)butyl)piperidin-4-ylmethyl)-2-methoxybenzamide

HRID 344380

반응식

HRID 344380 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(=O)([O-])[O-].[K+].[K+].BrCCCC[C:33]1[CH:43]=[CH:42][CH:41]=[C:35]2[C:36]([NH:38][C:39](=[O:40])[C:34]=12)=[O:37].[C:44]1(C)[CH:49]=CC=[CH:46][CH:45]=1>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]([CH2:49][CH2:44][CH2:45][CH2:46][N:38]3[C:39](=[O:40])[C:34]4[C:35](=[CH:41][CH:42]=[CH:43][CH:33]=4)[C:36]3=[O:37])[CH2:15][CH2:16]2)=[O:8])=[C:5]([O:20][CH3:21])[CH:4]=1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 21960043BromobutylphthalimideHCID 667809414-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride

생성물 1

HCID 539169944-Amino-5-chloro-N-(1-(4-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)butyl)piperidin-4-ylmethyl)-2-methoxybenzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride (15.0 g) was dissolved in dimethylformamide (100 ml) and toluene (150 ml). Potassium carbonate (18.6 g) and 4-bromobutylphthalimide (12.7 g) were added, and the mixture was stirred at 70 ° C. for 2 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 13.6 g of 4-amino-5-chloro-N-(1-(4-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)butyl)-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-278bfdb456fc497e9df5f8fc95d730d4
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05864039

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