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

HRID 55327노트

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HRID 55327 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-312a7754477f4b8aade832d48ac82f79
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624948

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