Diisopropylethylamine → HCID 118513278, compound

HRID 1478818Notes

Reaction equation

HRID 1478818 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH3:14])=[C:12]([C:15]([OH:17])=O)[N:11]=[N:10]2)=[CH:5][CH:4]=1.[NH2:18][C:19]1[C:20](=[O:32])[N:21]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[N:22]([CH3:25])[C:23]=1[CH3:24].C(N(CC)C(C)C)(C)C>C(Cl)Cl.CO>[CH:26]1([N:21]2[C:20](=[O:32])[C:19]([NH:18][C:15]([C:12]3[N:11]=[N:10][N:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[C:13]=3[CH3:14])=[O:17])=[C:23]([CH3:24])[N:22]2[CH3:25])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 7283161-(4-METHOXY-PHENYL)-5-METHYL-1H-[1,2,3]TRIAZOLE-4-CARBOXYLIC ACIDHCID 612730214-amino-2-cyclohexyl-1,5-dimethyl-2,3-dihydro-1H-pyrazol-3-one2×

Product 1

HCID 118513278HCID 118513278, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a vial was added 1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (0.040 g, 0.170 mmol) and a solution of Ghosez reagent (0.047 ml, 0.340 mmol) in DCM (0.95 ml). The mixture was sonicated and heated to aid dissolution. The vial was placed on the IKA shaker for 4 hours. To this mixture was added a solution of 4-amino-2-cyclohexyl-1,5-dimethyl-1H-pyrazol-3(2H)-one (Intermediate A) (10.043 g, 0.204 mmol) and N,N-diisopropylethylamine (0.030 ml, 0.170 mmol) in DCM (0.97 ml) and the vial was shaken for 16 hrs. A few drops of MeOH were added and the solvent was removed using a Genevac HT-4X evaporator. The crude mixture was purified by reverse phase chromatography and the product fraction was concentrated using a Genevac HT-4X evaporator. The crude product was dissolved in MeOH (1 ml) and eluted through a SiCO3 cartridge using MeOH as the eluent. The collected eluent was concentrated to give the title compound.

Workup

  1. customThe mixture was sonicated
  2. temperatureheated
  3. dissolutiondissolution
  4. customthe solvent was removed
  5. customa Genevac HT-4X evaporator
  6. customThe crude mixture was purified by reverse phase chromatography
  7. concentrationthe product fraction was concentrated
  8. customa Genevac HT-4X evaporator
  9. dissolutionThe crude product was dissolved in MeOH (1 ml)
  10. washeluted through a SiCO3 cartridge
  11. concentrationThe collected eluent was concentrated

Sources & evidence

ORD record
ord-64e4670566cb42feb8311a2b92818794
Source dataset
uspto-grants-2016_08
Patent number
US09403833B2

Reaction notes

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