Cyclohexylamine → HCID 59830671, compound

HRID 1187373Notes

Reaction equation

HRID 1187373 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-e65e372a35464766be238246b8ef5a49
Source dataset
uspto-grants-2014_03
Patent number
US08673938B2

Reaction notes

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