Potassium Carbonate → (5R)-3-{6-[(3,3-dimethyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-3-pyridinyl}-5-ethyl-5-methyl-2,4-imidazolidinedione

HRID 527717ノート

反応式

HRID 527717 の反応式
[CH3:1][C:2]1([CH3:12])[C:6]2[C:7]([OH:11])=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1.Cl[C:14]1[N:19]=[CH:18][C:17]([N:20]2[C:24](=[O:25])[C@:23]([CH2:27][CH3:28])([CH3:26])[NH:22][C:21]2=[O:29])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:12])[C:6]2[C:7]([O:11][C:14]3[N:19]=[CH:18][C:17]([N:20]4[C:24](=[O:25])[C@:23]([CH2:27][CH3:28])([CH3:26])[NH:22][C:21]4=[O:29])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 685333883,3-dimethyl-1H-isobenzofuran-4-ol2 回HCID 86698458(5R)-3-(6-chloro-3-pyridinyl)-5-ethyl-5-methyl-2,4-imidazolidinedione2 回

生成物 1

HCID 57411186(5R)-3-{6-[(3,3-dimethyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-3-pyridinyl}-5-ethyl-5-methyl-2,4-imidazolidinedione収率 45.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

3,3-Dimethyl-1,3-dihydro-2-benzofuran-4-ol (Intermediate 193, 68 mg, 0.4 mmol) and (5R)-3-(6-chloropyridin-3-yl)-5-ethyl-5-methylimidazolidine-2,4-dione (Intermediate 194, 126 mg, 0.48 mmol) were dissolved in DMF (1.0 mL) and K2CO3 (143 mg, 1.03 mmol) was added. The resulting suspension was heated to 130° C. under microwave irradiation for 40 minutes. The reaction mixture was diluted with water (25 mL) and ethyl acetate (25 mL), and then two phases were separated. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash chromatography (Biotage system) on silica gel using cyclohexane/ethyl acetate 50:50 as eluent affording the title compound (70 mg) as a white solid.

後処理

  1. customtwo phases were separated
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by flash chromatography (Biotage system) on silica gel

出典と根拠

ORDレコード
ord-1dc3d327d3c445d58faaf63d3440e725
出典データセット
uspto-grants-2016_05
特許番号
US09346790B2

反応ノート

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