Isobutylamine → Methyl 5-(3-isobutylureido)-1-methyl-1H-pyrazole-3-carboxylate

HRID 541429Notes

Reaction equation

HRID 541429 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:3]=1.ClC(Cl)(O[C:16](=[O:22])OC(Cl)(Cl)Cl)Cl.CCN(C(C)C)C(C)C.[CH2:33]([NH2:37])[CH:34]([CH3:36])[CH3:35]>C1COCC1>[CH2:33]([NH:37][C:16](=[O:22])[NH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:3]=1)[CH:34]([CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 6558IsobutylamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 13324840methyl 5-amino-1-methyl-1H-pyrazole-3-carboxylate2×

Product 1

HCID 68288869Methyl 5-(3-isobutylureido)-1-methyl-1H-pyrazole-3-carboxylateYield 168.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-amino-1-methyl-1H-pyrazole-3-carboxylate (compound 351.4, 0.088 g, 0.57 mmol) in THF (5 ml) was added triphosgene (0.084 g, 0.28 mmol) followed by DIEA (0.2 ml, 1.14 mmol). After the mixture was stirred at room temperature for 2 hours, isobutyl amine (0.225 ml, 2.28 mmol) was added. The resulting mixture was stirred at room temperature over night. The mixture was partitioned between water and EtOAc. The EtOAc layer was washed with 1 M aqueous NaH2PO4 solution followed by brine, dried with Na2SO4, and concentrated to give 120 mg (83%) of a light yellow solid. m/z (ES+) 255 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred at room temperature over night
  2. customThe mixture was partitioned between water and EtOAc
  3. washThe EtOAc layer was washed with 1 M aqueous NaH2PO4 solution
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5d0789d6e7cb4463973533883e8cb8a2
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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