Potassium Carbonate → 2-[1-(Cyclopropylmethyl)piperidin-4-yl]-7-(2,4-dichlorophenyl)[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one hydrochloride

HRID 2088679Notes

Reaction equation

HRID 2088679 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[C:10]1[NH:15][C:14](=[O:16])[N:13]2[N:17]=[C:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[N:19]=[C:12]2[CH:11]=1.Br[CH2:27][CH:28]1[CH2:30][CH2:29]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:2].[CH:28]1([CH2:27][N:23]2[CH2:24][CH2:25][CH:20]([C:18]3[N:19]=[C:12]4[N:13]([C:14](=[O:16])[NH:15][C:10]([C:4]5[CH:5]=[CH:6][C:7]([Cl:9])=[CH:8][C:3]=5[Cl:2])=[CH:11]4)[N:17]=3)[CH2:21][CH2:22]2)[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 1363378137-(2,4-Dichlorophenyl)-2-(piperidin-4-yl)[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one hydrochloride

Product 1

HCID 1363378142-[1-(Cyclopropylmethyl)piperidin-4-yl]-7-(2,4-dichlorophenyl)[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1.00 g (2.50 mmol) of 7-(2,4-dichlorophenyl)-2-(piperidin-4-yl)[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one hydrochloride were initially charged in DMF (6 ml), and 268 μl (2.75 mmol) of 1-bromomethylcyclopropane and 759 mg (5.49 mmol) of potassium carbonate were added. The reaction mixture was stirred at 80° C. for 16 h, the solution was then filtered and ethyl acetate (100 ml) and water (75 ml) were added. The phases were separated and the aqueous phase was extracted with ethyl acetate (two times 15 ml). The combined organic phases were washed with saturated aqueous sodium chloride solution, dried (magnesium sulfate) and concentrated. The product was taken up in acetonitrile and purified by preparative RP-HPLC (Method 11). This gave 413 mg (39% of theory) of the product.

Workup

  1. filtrationthe solution was then filtered
  2. additionethyl acetate (100 ml) and water (75 ml) were added
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (two times 15 ml)
  5. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated
  8. custompurified by preparative RP-HPLC (Method 11)

Sources & evidence

ORD record
ord-cd39597a7f124736b976de334084946b
Source dataset
uspto-grants-2013_05
Patent number
US08436003B2

Reaction notes

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