Cesium carbonate → HCID 58012174, compound

HRID 660946

Reaction equation

HRID 660946 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11](=[O:13])[N:10]([CH2:14][C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])=[O:16])[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:36][CH2:37][Cl:38]>C1(C)C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O.C(OCC)(=O)C>[Cl:38][CH2:37][CH2:36][N:12]1[C:11](=[O:13])[N:10]([CH2:14][C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:26])([F:27])[F:28])=[O:16])[N:9]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 1364381-Chloro-2-iodoethaneHCID 1361991092-[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[2-(tri-fluoromethyl)benzyl]-acetamide

Product 1

HCID 58012174HCID 58012174, compound

Reagents, catalysts & solvents 4

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

500 mg (1.01 mmol) of 2-[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[2-(trifluoromethyl)benzyl]-acetamide from Example 243A are dissolved in 10 ml of toluene with 230 mg (1.01 mmol) of benzyltriethylammonium chloride. Next, a solution of 658 mg (2.02 mmol) of caesium carbonate, dissolved in 1.0 ml water, is added, and the mixture vigorously stirred at RT for 30 mins. After addition of 1.92 g (10.13 mmol) of 1-iodo-2-chloroethane, the mixture is heated for 7 hrs at 80° C. with vigorous stirring. The suspension is then diluted with ethyl acetate and washed once each with water, 10% sodium thiosulphate and saturated ammonium chloride solution. The organic phase is dried over sodium sulphate, filtered and concentrated in vacuo. The crude product is purified by preparative HPLC [Method 9]. 195 mg (41% of theory) of the target compound are thus obtained.

Workup

  1. additionis added
  2. temperaturethe mixture is heated for 7 hrs at 80° C. with vigorous stirring
  3. washwashed once each with water, 10% sodium thiosulphate and saturated ammonium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by preparative HPLC [Method 9]
  8. custom195 mg (41% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-58b966efd83d47ffb5ab1a4a392881fc
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Linked notes

Loading…