Pyridine → N-[6-(5-methyl-2-furyl)-5-pyridin-4-ylpyrazin-2-yl]cyclopropanecarboxamide

HRID 1710698ノート

反応式

HRID 1710698 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]2[N:12]=[C:11]([NH2:13])[CH:10]=[N:9][C:8]=2[C:14]2[CH:19]=[CH:18]C=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[CH:20]1([C:23](Cl)=[O:24])[CH2:22][CH2:21]1.[N:26]1C=CC=CC=1>>[CH3:1][C:2]1[O:6][C:5]([C:7]2[N:12]=[C:11]([NH:13][C:23]([CH:20]3[CH2:22][CH2:21]3)=[O:24])[CH:10]=[N:9][C:8]=2[C:14]2[CH:15]=[CH:16][N:26]=[CH:18][CH:19]=2)=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 684967096-(5-Methylfuran-2-yl)-5-phenylpyrazin-2-ylamine

生成物 1

HCID 16071777N-[6-(5-methyl-2-furyl)-5-pyridin-4-ylpyrazin-2-yl]cyclopropanecarboxamide収率 81%

反応条件

温度
70 °C

実験手順

To a stirred solution of 6-(5-methylfuran-2-yl)-5-phenylpyrazin-2-ylamine (42 mg, 0.166 mmol) in pyridine (1.8 mL) was added cyclopropanecarbonyl chloride (38 μL, 0.41 mmol). The solution was stirred at 70° C. for 6 h, evaporated, partitioned between dichloromethane and a 4% sodium bicarbonate aqueous solution, the aqueous phase extracted twice with dichloromethane, the organic layers washed with brine, dried (MgSO4) and evaporated. The residue was triturated with diethyl ether and methanol and the precipitate was collected by filtration and dried to furnish the title compound as a brown solid (43 mg, 81%).

後処理

  1. customevaporated
  2. custompartitioned between dichloromethane
  3. extractiona 4% sodium bicarbonate aqueous solution, the aqueous phase extracted twice with dichloromethane
  4. washthe organic layers washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was triturated with diethyl ether and methanol
  8. filtrationthe precipitate was collected by filtration
  9. customdried

出典と根拠

ORDレコード
ord-030fcc4946d143919220c11a66c81904
出典データセット
uspto-grants-2010_09
特許番号
US07790728B2

反応ノート

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