Cyclohexylamine → HCID 59830716, compound

HRID 1187368Notes

Reaction equation

HRID 1187368 reaction equation
[CH3:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.O[N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2N=N1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.C1(N)CCCCC1>ClCCl>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([NH:13][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:16]2)=[O:6])=[C:2]([CH3:1])[N:10]=1

Participants

7

Reactant 5

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 462238396-Chloro-2-methylpyridine-3-carboxylic acid

Product 1

HCID 59830716HCID 59830716, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-methyl-6-chloronicotinic acid (300 mg, 1.75 mmol) and 1-hydroxybenzotriazole (260 mg, 1.92 mmol) was stirred in dichloromethane (25 ml) then triethylamine (561 ul, 4.02 mmol) and EDAC (401 mg, 2.1 mmol) were added and stirred for 5 minutes then cyclohexylamine (201 ul, 1.75 mmol) was added and the reaction was stirred for a further 16 hours at room temperature. The reaction was diluted with dichloromethane (25 ml), washed with sat. NaHCO3, 1M HCl, water, brine and dried over MgSO4, filtered and the solvent evaporated to give 6-chloro-2-methyl-N-cyclohexylnicotinamide (340 mg, 77%) as a fawn coloured powder

Workup

  1. stirringthe reaction was stirred for a further 16 hours at room temperature
  2. washwashed with sat. NaHCO3, 1M HCl, water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-3d21edef8e4a4b55aff2ed12705db533
Source dataset
uspto-grants-2014_03
Patent number
US08673938B2

Reaction notes

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