Potassium Carbonate → HCID 118235984, compound

HRID 1771394Notes

Reaction equation

HRID 1771394 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11].CNC1CCCCC1NC.[C:25]([C:29]1[CH:33]=[C:32]([NH2:34])[NH:31][N:30]=1)([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[NH2:34][C:32]1[N:31]([C:2]2[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=2)[CH2:5][N:6]2[CH2:10][CH2:9][CH2:8][C:7]2=[O:11])[N:30]=[C:29]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:33]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 90001880HCID 90001880, compoundHCID 178441179HCID 178441179, compound

Product 1

HCID 118235984HCID 118235984, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1-(3-iodobenzyl)pyrrolidin-2-one (5.49 g, 16.8 mmol) in toluene (20 mL) was added N1,N2-dimethylcyclohexane-1,2-diamine (530 μL, 3.40 mmol), 3-(tert-butyl)-1H-pyrazol-5-amine (2.57 g, 18.5 mmol), potassium carbonate (4.64 g, 33.5 mmol) and copper(I) iodide (160 mg, 0.839 mmol), and the reaction mixture was heated to 110° C. for 3 days. The mixture was cooled to RT and was partitioned between water (50 mL) and EtOAc (100 mL). The organic phase was separated and was washed with water (4×50 mL) and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 120 g, 0-50% EtOAc in isohexane, gradient elution) to afford the title compound, Intermediate A16, as a black gum (1.64 g, 30%); Rt 1.43 min (Method 2, acidic); m/z 313 (M+H)+, (ES+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. customwas partitioned between water (50 mL) and EtOAc (100 mL)
  3. customThe organic phase was separated
  4. washwas washed with water (4×50 mL)
  5. customdried
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, 120 g, 0-50% EtOAc in isohexane, gradient elution)

Sources & evidence

ORD record
ord-da84338d18144d05a7559d4c55364d8b
Source dataset
uspto-grants-2016_02
Patent number
US09249125B2

Reaction notes

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