Cyclopropanecarbonyl chloride → N-(6-Chloro-5-pyridin-4-ylpyrazin-2-yl)cyclopropanecarboxamide

HRID 1710681Notes

Reaction equation

HRID 1710681 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[N:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1.[CH:15]1([C:18](Cl)=[O:19])[CH2:17][CH2:16]1>N1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:18]([CH:15]2[CH2:17][CH2:16]2)=[O:19])[CH:5]=[N:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 594576006-Chloro-5-pyridin-4-ylpyrazin-2-amine

Product 1

HCID 59457608N-(6-Chloro-5-pyridin-4-ylpyrazin-2-yl)cyclopropanecarboxamideYield 70.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 6-chloro-5-pyridin-4-ylpyrazin-2-amine (Preparation 7, 0.73 g, 3.56 mmol) in pyridine (15 mL) was added cyclopropanecarbonyl chloride (648 μL, 7.1 mmol). The solution was stirred at 70° C. for 1 h 30 min, 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 light brown solid (0.69 g, 70%).

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-bc128fb6fdaa4d6ea7a2be3f8bbf40ef
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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