Citric Acid → Ethyl[5-(3,5-difluorophenyl)-5-methyl-2,4-dioxo-3-pyridin-2-ylimidazolidin-1-yl]acetate

HRID 1685382노트

반응식

HRID 1685382 반응식
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]1[C:10]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)([CH3:11])[C:9](=[O:20])[NH:8][C:7]1=[O:21])[CH3:2].[NH2:23][C:24]1C=[CH:28][CH:27]=[CH:26][CH:25]=1.BrC1C=CC=CN=1.C([O-])(=O)C.[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1.[Cu].[Cu]Cl.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]1[C:10]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)([CH3:11])[C:9](=[O:20])[N:8]([C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[C:7]1=[O:21])[CH3:2]

참가 물질

10

반응물 5

HCID 311Citric AcidHCID 6115AnilineHCID 79732-BromopyridineHCID 517044Potassium AcetateHCID 91574597Ethyl[5-(3,5-difluorophenyl)-5-methyl-2,4-dioxoimidazolidin-1-yl]acetate

생성물 1

HCID 123216751Ethyl[5-(3,5-difluorophenyl)-5-methyl-2,4-dioxo-3-pyridin-2-ylimidazolidin-1-yl]acetate

시약·촉매·용매 4

HCID 23978Copper촉매HCID 62652Cuprous chloride촉매HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

A stirred solution of ethyl[5-(3,5-difluorophenyl)-5-methyl-2,4-dioxoimidazolidin-1-yl]acetate, isomer A (100 mg, 0.320 mmol, described in Intermediate 7), 2-bromopyridine (0.156 mL, 1.60 mmol), copper powder (71.2 mg, 1.12 mmol), copper (I) chloride (6.34 mg, 0.064 mmol), and potassium acetate (94.0 mg, 0.961 mmol) in pyridine (1.8 mL) was heated at 100° C. for 18 h. The cooled reaction mixture was poured onto 10% citric acid (20 mL) and with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 50:50, to provide the title compound. MS: m/z=390 (M+1).

후처리

  1. customThe cooled reaction mixture
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with a gradient of hexane

출처 및 근거

ORD 기록
ord-cfcf6faedb6b4c98a25f17fd6a0d0008
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148390B2

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