Hydrochloric Acid → 5-(4-chlorophenyl)-N-(2-cyclohexyl-2-oxoethyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide

HRID 254835Notes

Reaction equation

HRID 254835 reaction equation
[CH:1]1([C:7](=[O:17])[CH2:8][NH:9][C:10](=[O:16])OC(C)(C)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.Cl.NCC(C1CCCCC1)=O.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:41]([C:42]3[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][C:43]=3[Cl:49])[N:40]=[C:39](C(O)=O)[C:38]=2[CH3:53])=[CH:33][CH:32]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.O1CCOCC1.CN(C=O)C>[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]2[N:41]([C:42]3[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][C:43]=3[Cl:49])[N:40]=[C:39]([C:10]([NH:9][CH2:8][C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[O:17])=[O:16])[C:38]=2[CH3:53])=[CH:35][CH:36]=1

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 15194215-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acidHCID 222816062-Amino-1-cyclohexylethan-1-one hydrochlorideHCID 58430272tert-butyl N-(2-cyclohexyl-2-oxoethyl)carbamate

Product 1

HCID 668447715-(4-chlorophenyl)-N-(2-cyclohexyl-2-oxoethyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamideYield 49%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a tert-butyl 2-cyclohexyl-2-oxoethylcarbamate (228 mg, 0.946 mmol) in DCM (5 mL) was added 4M HCl in 1,4-dioxane (5 mL) at room temperature. The reaction continued for an hour at room temperature. The volatiles were removed under vacuum. To the residue (2-amino-1-cyclohexylethanone hydrochloric acid), 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid (361 mg, 0.946 mmol), EDCI (272 mg, 1.429 mmol), HOBt (192 mg, 1.429 mmol) in DMF (9 mL) was added NMM (1.0 mL, 9.46 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight. The residue was purified by reverse-phase prep HPLC to afford the title compound (232 mg, 49%).

Workup

  1. waitThe reaction continued for an hour at room temperature
  2. customThe volatiles were removed under vacuum
  3. customThe residue was purified by reverse-phase prep HPLC

Sources & evidence

ORD record
ord-295dea42246b4d318587c133dab8c614
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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