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 344278

반응식

HRID 344278 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17].Cl.Cl.[NH2:20][C:21]1[C:36]([Cl:37])=[CH:35][C:24]([C:25]([NH:27][CH2:28][CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:26])=[C:23]([O:38][CH3:39])[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:20][C:21]1[C:36]([Cl:37])=[CH:35][C:24]([C:25]([NH:27][CH2:28][CH:29]2[CH2:30][CH2:31][N:32]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]3[C:11](=[O:12])[C:10]4[C:9](=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:8]3=[O:17])[CH2:33][CH2:34]2)=[O:26])=[C:23]([O:38][CH3:39])[CH:22]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 136770N-(5-Bromopentyl)phthalimideHCID 699663304-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride

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 57.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N-(5-Bromopentyl)phthalimide (60 g) was added to a solution of 4-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (75.1 g) and potassium carbonate (112 g) in dimethylformamide (800 ml), and the mixture was stirred at 75°-80° C. for 8 hr. Insoluble matter was filtered off and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to give 60.2 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. filtrationInsoluble matter was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

출처 및 근거

ORD 기록
ord-32795de70aa447feaddbef816d19b4ea
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05864039

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