Cyclohexylamine → HCID 59516147, compound

HRID 1160533Notes

Reaction equation

HRID 1160533 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, compound

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 stiffed at ambient temperature for 4 h and then evaporated under reduced pressure. The residue was 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. dissolutionThe residue was dissolved in DCM (5 mL)
  3. customseparating
  4. filtrationfilter
  5. customThe product was recovered from the filtrate by flash column chromatography (SiO2, elution gradient 0-100% EtOAc in isohexane)
  6. customevaporated

Sources & evidence

ORD record
ord-809ca7a5157a445faf590548ea5cee9f
Source dataset
uspto-grants-2010_10
Patent number
US07816391B2

Reaction notes

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