2-Cyclohexylbenzenamine → N-2-cyclohexylphenyl-3-(3-chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-amide

HRID 1443842Notes

Reaction equation

HRID 1443842 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][C:14]([C:17]([OH:19])=O)=[N:13][C:12]=23)[CH:5]=[CH:6][CH:7]=1.C1([C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[NH2:28])CCCCC1.N1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O>[CH2:26]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:27]1[NH:28][C:17]([C:14]1[CH:15]=[CH:16][N:11]2[N:10]=[C:9]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[C:12]2[N:13]=1)=[O:19]

Participants

7

Reactant 4

HCID 4078992-CyclohexylbenzenamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 586287193-(3-Chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acidHCID 178418385HCID 178418385, compound

Product 1

HCID 68691514N-2-cyclohexylphenyl-3-(3-chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-amideYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(3-chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acid (0.08 g), 2-cyclohexylaniline (0.06 g), and 2 ml of N,N-dimethylformamide, 1-hyhdroxy benzotriazol (0.05 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.07 g) were added, and stirred at room temperature over 2 hours. The reactant was poured into 20 ml of water, and extracted with 80 ml of ethyl acetate. The extract was washed saturated saline solution, dried with magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate:toluene=1:1), and recrystallized with ethyl acetate to yield N-2-cyclohexylphenyl-3-(3-chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-amide (0.08 g, 64%) as a yellow needle crystal. mp: 160.2-161.4° C.

Workup

  1. additionwere added
  2. extractionextracted with 80 ml of ethyl acetate
  3. washThe extract was washed saturated saline solution
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:toluene=1:1)
  7. customrecrystallized with ethyl acetate

Sources & evidence

ORD record
ord-e568327d701745d7a22deed94269cc8a
Source dataset
uspto-grants-2010_02
Patent number
US07662826B2

Reaction notes

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