Potassium Carbonate → 2-(difluoromethyl)-1-[4-(3-methoxyprop-1-yn-1-yl)-6-(morpholin-4-yl)pyrimidin-2-yl]-1H-benzimidazole

HRID 1403149ノート

反応式

HRID 1403149 の反応式
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[CH:23]([F:25])[F:24])[N:3]=1.[CH3:26][O:27][CH2:28][C:29]#[CH:30].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O.[Cu]I.C(Cl)(Cl)Cl>[F:24][CH:23]([F:25])[C:15]1[N:14]([C:4]2[N:3]=[C:2]([C:30]#[C:29][CH2:28][O:27][CH3:26])[CH:7]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[N:5]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 693933-MethoxypropyneHCID 442492591-[4-chloro-6-(4-morpholinyl)-2-pyrimidinyl]-2-(difluoromethyl)-1H-benzimidazole

生成物 1

HCID 866867852-(difluoromethyl)-1-[4-(3-methoxyprop-1-yn-1-yl)-6-(morpholin-4-yl)pyrimidin-2-yl]-1H-benzimidazole

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

1-[4-Chloro-6-(morpholin-4-yl)pyrimidin-2-yl]-2-(difluoromethyl)-1H-benzimidazole (100 mg) was dissolved in dimethylformamide (1 mL), and 3-methoxyprop-1-yne (45 μL), tetrakistriphenylphosphine palladium (0) (16 mg), copper (I) iodide (1.3 mg), and potassium carbonate (227 mg) were added thereto, followed by stirring in a microwave reactor at 80° C. for 1 hour. An aqueous ammonium chloride solution and chloroform were added thereto, and the organic layer was extracted, washed with saturated brine, and then dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=60:40). A mixed solvent of diisopropyl ether and hexane was added thereto, and the resulting solid was collected by filtration and further washed with hexane to obtain 2-(difluoromethyl)-1-[4-(3-methoxyprop-1-yn-1-yl)-6-(morpholin-4-yl)pyrimidin-2-yl]-1H-benzimidazole (10 mg) as a yellow powder.

後処理

  1. extractionthe organic layer was extracted
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThen, the solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=60:40)
  6. additionA mixed solvent of diisopropyl ether and hexane was added
  7. filtrationthe resulting solid was collected by filtration
  8. washfurther washed with hexane

出典と根拠

ORDレコード
ord-39609f8d463b41a9b92442dc21b679aa
出典データセット
uspto-grants-2014_12
特許番号
US08912180B2

反応ノート

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