Potassium Phosphate, Dibasic → HCID 22125638, compound

HRID 1857972Notes

Reaction equation

HRID 1857972 reaction equation
Br[C:2]1[S:6][C:5]([NH2:7])=[N:4][N:3]=1.[C:8]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].OP([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:7][C:5]1[S:6][C:2]([N:18]2[CH2:17][CH2:16][N:15]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:20][CH2:19]2)=[N:3][N:4]=1

Participants

5

Reactant 3

HCID 24450Potassium Phosphate, DibasicHCID 143452tert-Butyl piperazine-1-carboxylateHCID 36508832-Amino-5-bromo-1,3,4-thiadiazole

Product 1

HCID 22125638HCID 22125638, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (9.27 g), Boc-piperazine (11.51 g), and K2HPO4 (13.4 g) in 30 ml of DMF is heated at 100° C. under argon for four hours, then cooled and added to 100 g of ice. The mixture is extracted with ethyl acetate, and the organic phase washed twice with water and dried (MgSO4). Following removal of the solvent under reduced pressure, the residue is flash chromatographed on silica using 4% methanol in dichloromethane to afford 8.32 g of the title compound as a solid. Recrystallization from 240 ml of 1:1 acetonitrile-toluene provides 6.65 g of solid.

Workup

  1. temperaturecooled
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe organic phase washed twice with water
  4. dry with materialdried (MgSO4)
  5. customremoval of the solvent under reduced pressure
  6. customchromatographed on silica using 4% methanol in dichloromethane

Sources & evidence

ORD record
ord-193de3cff80b4363b0153423c96924f6
Source dataset
uspto-grants-2000_11
Patent number
US06150385

Reaction notes

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