Potassium Carbonate → HCID 10663447, compound

HRID 1600317Notes

Reaction equation

HRID 1600317 reaction equation
Cl[C:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:5][S:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[SH-:20].[Na+].[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:27][CH2:28][CH2:29]Cl>CN(C=O)C>[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:27][CH2:28][CH2:29][S:20][C:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:5][S:4][N:3]=1

Participants

6

Reactant 4

HCID 11430Potassium Carbonate2×HCID 104881643-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazoleHCID 16211346Sodium hydrosulfide hydrateHCID 21585204HCID 21585204, compound

Product 1

HCID 10663447HCID 10663447, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-(3-chloro-1,2,5-thiadiazol-4-yl)pyridine (2.0 g, 10.1 mmol)in DMF (10 ml) was cooled to 5° C. whereupon potassium carbonate (2.8 g, 20.2 mmol) and sodium hydrosulfide monohydrate (1.5 g, 20.2 mmol) were added to the reaction. Stirred for 1 h then potassium carbonate (1.4 g, 10.1 mmol) and a solution of 3-(2-thienyl)-1-chloropropane (1.8 g, 11.2mmol) in DMF (5 ml) were added to the reaction and stirred for 1 h at room temperature. The reaction was quenched with water then extracted with methylene chloride (3×75 ml). The organic phase was dried over NaCl/Na2SO4 then evaporated. The residue was purified by flash chromatography eluting with 1:1 ethyl acetate/hexanes to yield 1.0 g of 3-(3-(3-(2-thienyl)-1-propylthio)-1,2,5-thiadiazol-4-yl)pyridine. Quaternization and reduction was done as described in example 72. (Compound 133). M.p. 98°-100° C.

Workup

  1. additionwere added to the reaction
  2. stirringstirred for 1 h at room temperature
  3. customThe reaction was quenched with water
  4. extractionthen extracted with methylene chloride (3×75 ml)
  5. dry with materialThe organic phase was dried over NaCl/Na2SO4
  6. customthen evaporated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1e439b78c7c94937a28195a8797cd540
Source dataset
uspto-grants-1998_04
Patent number
US05744489

Reaction notes

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