Cyclohexylamine → HCID 59516147, compound

HRID 1799399Notes

Reaction equation

HRID 1799399 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]3[CH2:15][CH2:14]3)=[C:11]([C:16]([OH:18])=O)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:13]3[CH2:14][CH2:15]3)=[C:11]([C:16]([NH:31][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:18])[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 7965CyclohexylamineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 28606431HCID 28606431, compound2×

Product 1

HCID 59516147HCID 59516147, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1-(4-bromophenyl)-5-cyclopropyl-pyrazole-4-carboxylic acid (Intermediate #30) (237 mg, 0.77 mmol) was suspended in DCM (5 mL). One drop of DMF was added and then oxalyl chloride (200 μL, 2.32 mmol) was added slowly. The reaction mixture was stirred at ambient temperature for 4 h and then evaporated under reduced pressure. The residue was to dissolved in DCM (5 mL) and added to a solution of cyclohexylamine (97 μL, 0.85 mmol) and DIPEA (403 μL, 2.32 mmol) in DCM (5 mL). The mixture was stirred at ambient for 24 h and then water, (10 mL) was added and the mixture passed through a phase separating filter. The product was recovered from the filtrate by flash column chromatography (SiO2, elution gradient 0-100% EtOAc in isohexane). Pure fractions were combined and evaporated to give 1-(4-bromophenyl)-N-cyclohexyl-5-cyclopropyl-pyrazole-4-carboxamide as white solid. (277 mg, 92%)

Workup

  1. customevaporated under reduced pressure
  2. dissolutionto dissolved in DCM (5 mL)
  3. stirringThe mixture was stirred at ambient for 24 h
  4. customseparating
  5. filtrationfilter
  6. customThe product was recovered from the filtrate by flash column chromatography (SiO2, elution gradient 0-100% EtOAc in isohexane)
  7. customevaporated

Sources & evidence

ORD record
ord-de0ed89739754a598c02982667df7507
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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