Cesium carbonate → 2-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-[4-(2-methoxy-ethyl)-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl]-benzamide

HRID 1790283Notes

Reaction equation

HRID 1790283 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([N:20]2[C:24](=[O:25])[NH:23][CH: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+].[CH3:32][O:33][CH2:34][CH2:35]Br>CS(C)=O.O>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([N:20]2[C:24](=[O:25])[N:23]([CH2:35][CH2:34][O:33][CH3:32])[CH:22]=[N:21]2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1)=[O:5]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 135492557HCID 135492557, compound

Product 1

HCID 99320472-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-[4-(2-methoxy-ethyl)-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl]-benzamideYield 34.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A slurry of 2-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)-benzamide (44.4 mg, 0.122 mmol) and Cs2CO3 (66.0 mg, 0.202 mmol) were stirred in DMSO (0.813 mL) at ambient temperature for 20 minutes. 2-Bromoethyl methyl ether (17.0 mg, 0.122 mmol) was added and the reaction stirred at ambient temperature for 48 hours. The reaction was diluted with water (15-fold) and the aqueous extracted with CH2Cl2 (3×). The organics were dried over sodium sulfate, and concentrated in vacuo. The crude was purified by reverse phase HPLC reverse phase HPLC using a (25–65% gradient of 0.1% formic acid in acetonitrile and 0.1% formic acid in water) (to give the title compound (18 mg). LCMS (m/z) 423.5 M+1.

Workup

  1. extractionthe aqueous extracted with CH2Cl2 (3×)
  2. dry with materialThe organics were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude was purified by reverse phase HPLC reverse phase HPLC

Sources & evidence

ORD record
ord-d7b0d0dd863f4f7a88433015679f4e3f
Source dataset
uspto-grants-2006_07
Patent number
US07071223B1

Reaction notes

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