Ethyl 4-cyclopropyl-2,4-dioxobutanoate → HCID 89444869, compound

HRID 1522530Notes

Reaction equation

HRID 1522530 reaction equation
[CH:1]1([N:4]2[C:8]([NH2:9])=[CH:7][C:6]([CH3:10])=[N:5]2)[CH2:3][CH2:2]1.[CH:11]1([C:14](=O)[CH2:15][C:16](=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1>C(O)(=O)C>[CH:1]1([N:4]2[C:8]3[N:9]=[C:14]([CH:11]4[CH2:12][CH2:13]4)[CH:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7]=3[C:6]([CH3:10])=[N:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 16779961Ethyl 4-cyclopropyl-2,4-dioxobutanoateHCID 89444921HCID 89444921, compound

Product 1

HCID 89444869HCID 89444869, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-cyclopropyl-3-methyl-1H-pyrazol-5-amine (300 mg, 2.187 mmol), ethyl 4-cyclopropyl-2,4-dioxobutanoate (403 mg, 2.187 mmol) and acetic Acid (40 mL) were heated at reflux for 2 hours. The solvent was removed in vacuo and the crude residue was purified via silica gel chromatography (eluent: 0 to 11% EtOAc:Hex). The product was collected as 310 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.05-1.13 (m, 4 H), 1.16-1.21 (m, 2 H), 1.25-1.30 (m, 2 H), 1.46 (t, J=7.20 Hz, 3 H), 2.16-2.31 (m, 1 H), 2.63 (s, 3 H), 3.78 (m, J=7.26, 7.26, 3.79, 3.66 Hz, 1 H), 4.47 (q, J=7.24 Hz, 2 H), 7.40 (s, 1 H). LCMS(ES) [M+H]+ 286.2

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was removed in vacuo
  3. customthe crude residue was purified via silica gel chromatography (eluent: 0 to 11% EtOAc:Hex)
  4. customThe product was collected as 310 mg

Sources & evidence

ORD record
ord-bdedff66706d49499c084a87239427ca
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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