Cyclohexylamine → HCID 59830671, compound

HRID 2424912Notes

Reaction equation

HRID 2424912 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([CH:11]2[CH2:13][CH2:12]2)[N:3]=1.[CH:14]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(C(C)C)C(C)C)C>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:20][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:7])=[C:4]([CH:11]2[CH2:13][CH2:12]2)[N:3]=1

Participants

6

Reactant 3

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 86624328HCID 86624328, compound

Product 1

HCID 59830671HCID 59830671, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-chloro-2-cyclopropylnicotinoyl chloride (patent WO2005/080342) (0.216 g, 1 mmol) in DCM (2.5 mL) was added drop wise to a stirred solution of cyclohexylamine (0.171 mL, 1.50 mmol) and N-ethyldiisopropylamine (0.606 mL, 3.50 mmol) in THF (5 mL) at 20° C., over a period of 2 minutes under nitrogen. The resulting solution was stirred at room temperature for 2 hours. The reaction mixture was diluted with DCM (10 mL) and washed sequentially with 2M HCl (10 mL), saturated NaHCO3 (10 mL), and saturated brine (10 mL). The organic layer was collected from a phase separation cartridge (15 ml) and evaporated to afford crude product. This was triturated with Et2O to give a solid that was collected by filtration and dried under vacuum to give 6-chloro-N-cyclohexyl-2-cyclopropylnicotinamide (79%) as a white solid.

Workup

  1. washwashed sequentially with 2M HCl (10 mL), saturated NaHCO3 (10 mL), and saturated brine (10 mL)
  2. customThe organic layer was collected from a phase separation cartridge (15 ml)
  3. customevaporated
  4. customto afford crude product
  5. customThis was triturated with Et2O
  6. customto give a solid
  7. filtrationthat was collected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-63f43e63036b46808fa915e412f9e442
Source dataset
uspto-grants-2011_06
Patent number
US07964618B2

Reaction notes

Loading…