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

HRID 1710698Notes

Reaction equation

HRID 1710698 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
70 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-030fcc4946d143919220c11a66c81904
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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