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Methyl iodide → (RS)-2-(5,6-Difluoro-1-methyl-1H-benzoimidazol-2-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1367004
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HRID 1367004 반응식
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[CH2:16][C:17]1[NH:21][C:20]2[CH:22]=[C:23]([F:27])[C:24]([F:26])=[CH:25][C:19]=2[N:18]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].I[CH3:29]>CN(C)C=O.O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[CH2:16][C:17]1[N:18]([CH3:29])[C:19]2[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:20]=2[N:21]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 6328Methyl iodide3회HCID 24758Sodium hydride2회HCID 66968258(RS)-2-(5,6-Difluoro-1H-benzoimidazol-2-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 66968213(RS)-2-(5,6-Difluoro-1-methyl-1H-benzoimidazol-2-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 962Water
용매
HCID 6228Dimethylformamide용매

실험 절차

To a stirred suspension of sodium hydride (0.46 g, 60% dispersion in mineral oil) in dimethylformamide (30 ml) at 0° C., under argon, was added (RS)-2-(5,6-difluoro-1H-benzoimidazol-2-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester, D59 (2 g) and the reaction mixture stirred for a further 30 min. before the addition of iodomethane (0.78 ml). The reaction mixture was then stirred at room temperature for 18 h, a further equivalent of iodomethane (0.35 ml) was added and stirring continued for 24 h. Further portions of sodium hydride (0.23 g, 60% dispersion in mineral oil) and iodomethane (0.35 ml) were added and the reaction stirred for an additional 24 h. After diluting with water, the aqueous layer was extracted with diethyl ether (3×). The combined organics were dried (MgSO4) and solvent removed in vacuo to afford the title compound (0.5 g).

후처리

  1. stirringstirring
  2. waitcontinued for 24 h
  3. stirringthe reaction stirred for an additional 24 h
  4. extractionthe aqueous layer was extracted with diethyl ether (3×)
  5. dry with materialThe combined organics were dried (MgSO4) and solvent
  6. customremoved in vacuo

출처 및 근거

ORD 기록
ord-2aeb662529414420b7c03dbf652fac12
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07893090B2

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