Sodium Carbonate → 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-3-[(1-methyl-1H-benzimidazol-2-yl)methyl]dihydro-2H-pyran-2,4(3H)-dione

HRID 858764

반응식

HRID 858764 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]2([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[O:17][C:16](=[O:18])[CH2:15][C:14](=[O:19])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:32][C:33]1[N:37]([CH3:38])[C:36]2[CH:39]=[CH:40][CH:41]=[CH:42][C:35]=2[N:34]=1>COC(O)C(O)OC.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]2([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[O:17][C:16](=[O:18])[CH:15]([CH2:32][C:33]3[N:37]([CH3:38])[C:36]4[CH:39]=[CH:40][CH:41]=[CH:42][C:35]=4[N:34]=3)[C:14](=[O:19])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 2480442-(Chloromethyl)-1-methylbenzimidazoleHCID 160761096-(3-chloro-4-methoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione

생성물 1

HCID 587627306-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-3-[(1-methyl-1H-benzimidazol-2-yl)methyl]dihydro-2H-pyran-2,4(3H)-dione수율 7.5%

시약·촉매·용매 2

HCID 962Water용매HCID 21263609Dimethoxy ethylene glycol용매

반응 조건

온도
80 °C

실험 절차

6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione (127 mg, 0.362 mmol) was dissolved in a mixture of dimethoxy ethylene glycol (1.8 ml) and water (1.8 ml). The solution was heated to 80° C. Sodium carbonate (42.2 mg, 0.398 mmol) was then added to the mixture followed by 2-(chloromethyl)-1-methyl-1H-benzimidazole (42.2 mg, 0.398 mmol). The reaction mixture was stirred at 80° C. for 5 hrs, after which time the mixture was acidified to pH 5 and the product was extracted with ethyl acetate (3×25 ml). The combined organics were washed with brine (30 ml), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and purified by prep HPLC to afford the title compound as a white solid (13.5 mg).

후처리

  1. extractionthe product was extracted with ethyl acetate (3×25 ml)
  2. washThe combined organics were washed with brine (30 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompurified by prep HPLC

출처 및 근거

ORD 기록
ord-fc9778469d1f4a58a88a2cdcce549f91
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148226B2

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