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 2088679ノート

反応式

HRID 2088679 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cd39597a7f124736b976de334084946b
出典データセット
uspto-grants-2013_05
特許番号
US08436003B2

反応ノート

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