Cesium carbonate → 2-Chloro-N-((1-hydroxycycloheptyl)methyl)-5-[1-(2-hydroxyethyl)-5-methyl-1H-pyrazol-3-yl]benzamide

HRID 1988376노트

반응식

HRID 1988376 반응식
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]=[C:23]([CH3:25])[NH:22][N:21]=2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:33]([OH:35])[CH3:34]>CS(C)=O>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]=[C:23]([CH3:25])[N:22]([CH2:34][CH2:33][OH:35])[N:21]=2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 111875812-chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(5-methyl-1H-pyrazol-3-yl)-benzamideHCID 14202443Ethanol, 1-bromo-

생성물 1

HCID 114296462-Chloro-N-((1-hydroxycycloheptyl)methyl)-5-[1-(2-hydroxyethyl)-5-methyl-1H-pyrazol-3-yl]benzamide수율 58.9%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixture of 2-chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(5-methyl-1H-pyrazol-3-yl)-benzamide (5.0 g, 13.8 mmol) and cesium carbonate (9.0 g, 27.7 mmol) in dimethylsulfoxide (50 mL) was stirred at room temperature for 10 minutes. Bromoethanol (1.9 g, 15.2 mmol) was added and the resulting mixture was stirred at 80° C. for 12 h. The mixture was cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate (300 mL), washed with water and brine, dried, filtered and concentrated in vacuo. The residue was triturated with dichloromethane-ethyl acetate-diethyl ether (1:1:1, 100 mL) and washed with ethyl acetate to afford the title compound (3.3 g). LCMS (m/z) 406.1 M+1.

후처리

  1. stirringthe resulting mixture was stirred at 80° C. for 12 h
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. additionThe filtrate was diluted with ethyl acetate (300 mL)
  5. washwashed with water and brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with dichloromethane-ethyl acetate-diethyl ether (1:1:1, 100 mL)
  10. washwashed with ethyl acetate

출처 및 근거

ORD 기록
ord-5cb0e2a93f9744ca98e757e34af799ed
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553972B2

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