Potassium Iodide → 1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-methoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane

HRID 55327ノート

反応式

HRID 55327 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[N:18]2[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20][CH2:19]2)=[CH:4][CH:3]=1.[CH3:26][O:27][C:28]([CH2:30][CH2:31][C:32]1[CH:40]=[CH:39][C:35]([CH2:36][CH2:37]Br)=[CH:34][CH:33]=1)=[O:29].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[N:18]2[CH2:25][CH2:24][CH2:23][N:22]([CH2:37][CH2:36][C:35]3[CH:39]=[CH:40][C:32]([CH2:31][CH2:30][C:28]([O:27][CH3:26])=[O:29])=[CH:33][CH:34]=3)[CH2:21][CH2:20][CH2:19]2)=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 199575114-(2-Methoxycarbonylethyl)phenethyl bromideHCID 199575511-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane

生成物 1

HCID 199575241-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-methoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane収率 61.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane (12.1 g) in N,N-dimethylformamide (70 ml) were added 4-(2-methoxycarbonylethyl)phenethyl bromide (9.49 g), sodium carbonate (3.71 g) and potassium iodide (0.58 g), and the mixture was heated at 100° C. for 1 hour. The reaction mixture was poured into an ice-water (200 ml), and the mixture was extracted with methylene chloride (200 ml). The extract was washed with water, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on a silica gel column using a mixture of methylene chloride, diethyl ether and methanol (1:1:0.25) as eluent to give 1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-methoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane (11.38 g) as a colorless oily liquid.

後処理

  1. extractionthe mixture was extracted with methylene chloride (200 ml)
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by medium pressure liquid column chromatography on a silica gel column
  6. additiona mixture of methylene chloride, diethyl ether and methanol (1:1:0.25) as eluent

出典と根拠

ORDレコード
ord-312a7754477f4b8aade832d48ac82f79
出典データセット
uspto-grants-1997_04
特許番号
US05624948

反応ノート

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