Triethylamine → (2-{[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-methyl-butyrylamino]-methyl}-pyridin-3-yloxy)-acetic acid ethyl ester

HRID 1294603노트

반응식

HRID 1294603 반응식
Cl.Cl.[NH2:3][CH2:4][C:5]1[C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=[CH:7][N:6]=1.C(N(CC)CC)C.[CH3:25][C:26]([CH3:42])([N:31]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]1=[O:41])[CH2:27][C:28](O)=[O:29]>C(Cl)Cl>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][O:11][C:10]1[C:5]([CH2:4][NH:3][C:28](=[O:29])[CH2:27][C:26]([N:31]2[C:39](=[O:40])[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]2=[O:41])([CH3:42])[CH3:25])=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:17]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 22038564beta,beta-Dimethyl-1,3dioxo-2-isoindolinepropionic acidHCID 220385702-Aminomethyl-3-(ethoxycarbonylmethoxy)pyridine dihydrochloride

생성물 1

HCID 69158493(2-{[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-methyl-butyrylamino]-methyl}-pyridin-3-yloxy)-acetic acid ethyl ester수율 62.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-aminomethyl-3-(ethoxycarbonylmethoxy)pyridine dihydrochloride (610 mg, 2.155 mmol), triethylamine (732 μl, 5.258 mmol), N,N-dicyclohexylcarbodiimide (596 mg, 2.892 mmol) and 4-(N,N-diemethylamino)-pyridine (10 mg) in 6 ml of dry methylene chloride is added β,β-dimethyl-1,3-dioxo-2-isoindolinepropionic acid (650 mg, 2.629 mmol) at ambient temperature. The mixture is stirred for 24 hours. The precipitate of dicyclohexyl urea is filtered off. The filtrate is evaporated and the residue is purified via flash chromatography on silica gel using a methylene chloride/methylene chloride-ethanolic ammonia gradient (100 to 97:3) to give 591 mg of (2-{[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-methyl-butyrylamino]-methyl}-pyridin-3-yloxy)-acetic acid ethyl ester (46%).

후처리

  1. filtrationThe precipitate of dicyclohexyl urea is filtered off
  2. customThe filtrate is evaporated
  3. customthe residue is purified via flash chromatography on silica gel using a methylene chloride/methylene chloride-ethanolic ammonia gradient (100 to 97:3)

출처 및 근거

ORD 기록
ord-bd5853c213f4404b852cfa461ffc0e34
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241772B2

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