Cyclohexanecarboxylic acid → HCID 178428724, compound

HRID 254824Notes

Reaction equation

HRID 254824 reaction equation
CN1CCOCC1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])[N:18]=[C:17]([C:28](=[NH:31])[NH:29][OH:30])[C:16]=2[CH3:32])=[CH:11][CH:10]=1.[CH:33]1([C:39](O)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])[N:18]=[C:17]([C:28](=[NH:31])[NH:29][O:30][C:39]([CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[O:40])[C:16]=2[CH3:32])=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 7413Cyclohexanecarboxylic acidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178428726HCID 178428726, compound

Product 1

HCID 178428724HCID 178428724, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NMM (0.42 mL, 3.77 mmol) was added to a solution of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-hydroxy-4-methyl-1H-pyrazole-3-carboxamid amide (0.30 g, 0.75 mmol) obtained in Step 3, cyclohexylcarboxylic acid (97 mg, 0.75 mmol), HOBt (194 mg, 1.43 mmol) and EDCI (220 mg, 1.13 mmol) dissolved in DCM (7 mL). The mixture was stirred overnight at room temperature. After adding thereto EtOAc (30 mL), the mixture was successively washed with water, saturated NaHCO3 solution (20 mL) and brine (20 mL). The organic layer was isolated, dried over MgSO4, filtered, and concentrated under a vacuum, to obtain 5-(4-chlorophenyl)-N-(cyclohexanecarbonyloxy)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboximidamide as a white solid, which was used in the next step without further purification. The crude material was dissolved in pyridine (4 mL), and was subjected to microwave irradiation at 180° C. for 20 min., to remove volatile components under a vacuum. The residue was further purified by reverse phase preparative HPLC, to obtain the title compound as white solid (67 mg, 0.137 mmol, 18% via two steps).

Workup

  1. additionAfter adding
  2. washEtOAc (30 mL), the mixture was successively washed with water, saturated NaHCO3 solution (20 mL) and brine (20 mL)
  3. customThe organic layer was isolated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under a vacuum

Sources & evidence

ORD record
ord-51e7ed73996242de9482650003ae9105
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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