Dimethylformamide → 1-[(1-Carbomethoxy methoxy ethyl)-1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl]methanone

HRID 1769034노트

반응식

HRID 1769034 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11].[C:25]([CH2:29][O:30][CH2:31][CH2:32]Br)([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:25]([CH2:29][O:30][CH:31]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]1)=[O:11])[CH3:32])([O:27][CH3:28])=[O:26]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 183332351-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidineHCID 18946503Methyl (2-bromoethoxy)acetate

생성물 1

HCID 542868801-[(1-Carbomethoxy methoxy ethyl)-1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl]methanone

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

Mix [1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl]methanone (4.25 g, 12.91 mmol), carbomethoxy methoxy ethylbromide (3.01 g, 15.3 mmol), potassium carbonate (5.29 g, 38.25 mmol) and dimethylformamide (100 mL). Stir and heat and at 90° C. overnight. Allow to cool to room temperature, dilute with water and extract with ethyl acetate (2×). Wash the combined organic phases with water (3×), then brine and dry (MgSO4). Evaporate the solvent in vacuo to give and purify by chromatography to give the title compound.

후처리

  1. temperatureto cool to room temperature
  2. extractionextract with ethyl acetate (2×)
  3. washWash the combined organic phases with water (3×)
  4. dry with materialbrine and dry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. customto give
  7. custompurify by chromatography

출처 및 근거

ORD 기록
ord-9334016447e24a608f1a4d35e3b23c7b
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380731

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