Cesium carbonate → HCID 68709067, compound

HRID 1818779Notes

Reaction equation

HRID 1818779 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[Cl:20])[S:5]1(=[O:22])=[O:21].[CH3:23][C@H:24]1[CH2:29][NH:28][CH2:27][C@@H:26]([CH3:30])[NH:25]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(O)C>[ClH:20].[ClH:20].[Cl:20][C:14]1[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=1[N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:4]([CH2:3][CH2:2][N:28]2[CH2:27][C@H:26]([CH3:30])[NH:25][C@H:24]([CH3:23])[CH2:29]2)[S:5]1(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 68710766HCID 68710766, compound

Product 1

HCID 68709067HCID 68709067, compoundYield 128.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Step 2 0.20 g (0.5 mmol) of 1-(2-bromoethyl)-3-(2-chloro-4-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide, 0.09 g (0.75 mmol) of cis-2,6-dimethyl piperazine and 0.35 g (1 mmol) of cesium carbonate were dissolved in ethanol and heated to 90° C. for 30 hr. At the end of this time the solution was concentrated and the residue placed on a pad of silica gel eluting first with 20% ethyl acetate:hexane then 90% chloroform:methanol. The chloroform eluent was concentrated and the residue dissolved in ethanol, whereupon 2 mL of 2N HCl in ether added. The solution was concentrated to a smaller volume and triturated with ether and the solid removed by filtration to provide 0.11 g of 1-(2-chloro-4-fluorophenyl)-3-{2-[(3R,5S)-3,5-dimethylpiperazin-1-yl]ethyl}-1,3-dihydro-2,1,3-benzothiadiazole-2,2-dioxide dihydrochloride.

Workup

  1. concentrationAt the end of this time the solution was concentrated
  2. concentrationThe chloroform eluent was concentrated
  3. dissolutionthe residue dissolved in ethanol, whereupon 2 mL of 2N HCl in ether
  4. additionadded
  5. concentrationThe solution was concentrated to a smaller volume
  6. customtriturated with ether
  7. customthe solid removed by filtration

Sources & evidence

ORD record
ord-a63a42694ded44aea51c44564d679c3a
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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