Sodium Iodide → 3-({[4-({Cyclohexyl[2-(methoxymethyl)-5-(6-methoxypyridin-3-yl)furan-3-yl]methyl}amino)phenyl]carbonyl}amino)propanoic acid

HRID 1877090노트

반응식

HRID 1877090 반응식
Cl[CH:2]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[N:15][CH:16]=2)[O:6][C:7]=1[CH2:8][O:9][CH3:10].[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([NH:34][CH2:35][CH2:36][C:37]([O:39]CC)=[O:38])=[O:33])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CN(C)C(=O)C.O>[CH:19]1([CH:2]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]([NH:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[O:33])=[CH:30][CH:31]=2)[C:3]2[CH:4]=[C:5]([C:11]3[CH:16]=[N:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[O:6][C:7]=2[CH2:8][O:9][CH3:10])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 12469762Ethyl 3-(4-aminobenzamido)propanoateHCID 685124885-{4-[Chloro(cyclohexyl)methyl]-5-(methoxymethyl)furan-2-yl}-2-methoxypyridine

생성물 1

HCID 595293503-({[4-({Cyclohexyl[2-(methoxymethyl)-5-(6-methoxypyridin-3-yl)furan-3-yl]methyl}amino)phenyl]carbonyl}amino)propanoic acid수율 17.4%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

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온도
80 °C

실험 절차

A mixture of 5-{4-[chloro(cyclohexyl)methyl]-5-(methoxymethyl)furan-2-yl}-2-methoxypyridine (0.4 g), ethyl 3-{[(4-aminophenyl)carbonyl]amino}propanoate (0.3 g), sodium carbonate (0.2 g) and sodium iodide (0.2 g) in N,N-dimethylacetamide (10 mL) was stirred overnight at 80° C. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (25% ethyl acetate/hexane to 70% ethyl acetate/hexane). To the residue were added ethanol (2 mL), tetrahydrofuran (2 mL) and 1N lithium hydroxide (0.45 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and water (10 mL) was added. The mixture was neutralized with 1N hydrochloric acid under ice-cooling, and stirred for 1 hr. The resulting precipitate was collected by filtration and dried to give the title compound (104 mg, 16%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (25% ethyl acetate/hexane to 70% ethyl acetate/hexane)
  6. additionTo the residue were added ethanol (2 mL), tetrahydrofuran (2 mL) and 1N lithium hydroxide (0.45 mL)
  7. stirringthe mixture was stirred at room temperature for 1 hr
  8. customThe solvent was evaporated under reduced pressure, and water (10 mL)
  9. additionwas added
  10. temperaturecooling
  11. stirringstirred for 1 hr
  12. filtrationThe resulting precipitate was collected by filtration
  13. customdried

출처 및 근거

ORD 기록
ord-4ab02023b4d14a4db778bbf1aaab92d0
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309580B2

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