Cesium carbonate → 4-Imidazol-1-ylmethyl-2-[2-(2-oxo-piperidin-1-yl)-phenoxy]-benzonitrile

HRID 1594846

反応式

HRID 1594846 の反応式
F[C:2]1[CH:9]=[C:8]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[O:16]=[C:17]1[CH2:22][CH2:21][CH2:20][CH2:19][N:18]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[OH:29].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N:11]1([CH2:10][C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([O:29][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][C:17]3=[O:16])[CH:9]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 115066091-(2-Hydroxyphenyl)piperidin-2-oneHCID 21697068Benzonitrile, 2-fluoro-4-(1H-imidazol-1-ylmethyl)-

生成物 1

HCID 97996074-Imidazol-1-ylmethyl-2-[2-(2-oxo-piperidin-1-yl)-phenoxy]-benzonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

2-Fluoro-4-imidazol-1-ylmethyl-benzonitrile (as described in Step E above) (0.080 g, 0.4 mmol), 2-(2-oxo-piperidin-1-yl)-phenol (as described in Step F above) (0.091 g, 0.5 mmol) and cesium carbonate (0.261 g, 0.8 mmol) were combined in DMF (2.0 mL) and heated at 50° C. for 18 hr. The reaction mixture was partitioned between EtOAc and a minimum volume of H2O. Additional product was salted out from the aqueous layer with solid NaCl, and extracted into EtOAc. The organic layers were combined, dried (Na2SO4), filtered and concentrated to give the title compound after RP HPLC on a Waters Prep Pak column eluting with a 0.1% TFA/H2O: 0.1% TFA/CH3CN gradient followed by conversion to the free base.

後処理

  1. customThe reaction mixture was partitioned between EtOAc
  2. extractionextracted into EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-764d005d84154974a976aba09e644e7d
出典データセット
uspto-grants-2001_09
特許番号
US06284755B1

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