Triethylamine → 2-Chloro-5-(6-methyl-pyridin-3-yl)-N-(1-p-tolyl-cyclohexylmethyl)-benzamide

HRID 1988367Notes

Reaction equation

HRID 1988367 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:40]1([CH3:54])[CH:45]=[CH:44][C:43]([C:46]2([CH2:52][NH2:53])[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]2)=[CH:42][CH:41]=1.C(N(CC)CC)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[CH:7][C:3]=1[C:4]([NH:53][CH2:52][C:46]1([C:43]2[CH:42]=[CH:41][C:40]([CH3:54])=[CH:45][CH:44]=2)[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]1)=[O:6]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184386612-Chloro-5-(6-methylpyridin-3-yl)benzoic acidHCID 184387081-[1-(4-Methylphenyl)cyclohexyl]methanamine

Product 1

HCID 588181732-Chloro-5-(6-methyl-pyridin-3-yl)-N-(1-p-tolyl-cyclohexylmethyl)-benzamideYield 27.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-5-(6-methyl-pyridin-3-yl)-benzoic acid (73 mg, 0.29 mmol) in N,N-dimethylformamide (4 mL) was added sequentially, stirring at room temperature for 10 minutes after each addition, 1-hydroxybenzotriazole (48 mg, 0.35 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (62 mg, 0.32 mmol), C-(1-p-tolyl-cyclohexyl)-methylamine (60 mg, 0.29 mmol) and triethylamine (31 mg, 0.31 mmol). The mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by reverse phase chromatography to afford the title compound (35 mg). LCMS (m/z) 433.2 M+1.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 h
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-ce40cefca7a741209859a2c29031745e
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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