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

HRID 1988376Notes

Reaction equation

HRID 1988376 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5cb0e2a93f9744ca98e757e34af799ed
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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