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

HRID 1685382ノート

反応式

HRID 1685382 の反応式
[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]

参加物

10

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 23978Copper触媒HCID 62652Cuprous chloride触媒HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cfcf6faedb6b4c98a25f17fd6a0d0008
出典データセット
uspto-grants-2012_04
特許番号
US08148390B2

反応ノート

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