Triethylamine → 1-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]-3-carbamoyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 47527노트

반응식

HRID 47527 반응식
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].C([N:29]([CH2:32]C)CC)C.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:36]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]([C:32](=[O:36])[NH2:29])[C:18]3=[O:26])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 227452181-[1-(1-methoxycarbonylpiperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

생성물 1

HCID 98872931-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]-3-carbamoyl-1,3-dihydro-2H-benzimidazol-2-one수율 69.2%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

1-[1-(1-Methoxycarbonylpiperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one (49 mg) and 30 mg of triethylamine were dissolved in 4 ml of chloroform, and to which 30 mg of (4-nitrophenyl) chloroformate was added, followed by 30 minutes' stirring at room temperature. Thereafter the solvent was distilled off, and the resulting residue was dissolved in 5 ml of tetrahydrofuran. To the solution 1 ml of aqueous ammonia was added and stirred for 30 minutes at room temperature. Then water was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated and the resulting residue was purified by silica gel column chromatography (chloroform/methanol=20/1) to provide 38 mg of the title compound as a colorless solid.

후처리

  1. distillationThereafter the solvent was distilled off
  2. dissolutionthe resulting residue was dissolved in 5 ml of tetrahydrofuran
  3. additionTo the solution 1 ml of aqueous ammonia was added
  4. stirringstirred for 30 minutes at room temperature
  5. additionThen water was added to the reaction liquid
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol=20/1)

출처 및 근거

ORD 기록
ord-33d360d89b5744b48d6cb5db5891c71d
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699880B1

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