Ethanolamine → 3-(4-Chlorophenyl)-8-fluoro-7-(2-hydroxyethylamino)-2-isopropyl-chromen-4-one

HRID 14461노트

반응식

HRID 14461 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([F:20])[C:13](F)=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:21]([CH3:23])[CH3:22])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:31]([CH2:33][NH2:34])[OH:32]>CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([F:20])[C:13]([NH:34][CH2:33][CH2:31][OH:32])=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:21]([CH3:22])[CH3:23])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 68704522HCID 68704522, 화합물

생성물 1

HCID 687043963-(4-Chlorophenyl)-8-fluoro-7-(2-hydroxyethylamino)-2-isopropyl-chromen-4-one

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

A stirred solution of 3-(4-chlorophenyl)-7,8-difluoro-2-isopropyl-chromen-4-one (3.94 g, 11.8 mmol), triethylamine (2.4 g, 3.2 ml, 23.6 mmol, 2 eq.) and ethanolamine (0.72 g, 0.71 ml, 11.8 mmol, 1 eq.) in N,N-dimethylacetamide (200 ml) is heated at 150° C. overnight. The reaction mixture is allowed to cool to room temperature and the solvent is removed by evaporation in vacuo. The residue is dissolved in ethyl acetate and washed with 2M HCl solution. The organic layer is washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo to afford a brown oil. The oil is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:6) to afford the title compound.

후처리

  1. customthe solvent is removed by evaporation in vacuo
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with 2M HCl solution
  4. washThe organic layer is washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customto afford a brown oil
  9. customThe oil is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:6)

출처 및 근거

ORD 기록
ord-53cb518bd0a54f4e82fd9274a2a555d0
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732435B2

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