Methyl iodide → HCID 131736507, compound

HRID 1478222Notes

Reaction equation

HRID 1478222 reaction equation
[CH:1]([N:4]1[C:8](=[O:9])[C:7]([NH:10][C:11](=[O:27])[O:12][CH2:13][CH:14]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[C:6]([CH3:28])[NH:5]1)([CH3:3])[CH3:2].[CH3:29]I>CN(C=O)C>[CH:1]([N:4]1[C:8](=[O:9])[C:7]([NH:10][C:11](=[O:27])[O:12][CH2:13][CH:14]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[C:6]([CH3:28])[N:5]1[CH3:29])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 131736506HCID 131736506, compound

Product 1

HCID 131736507HCID 131736507, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (9H-fluoren-9-yl)methyl (2-isopropyl-5-methyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)carbamate (2.109 g, 5.59 mmol) in DMF (30 mL) was added methyl iodide (2.80 mL, 44.7 mmol). The reaction mixture was stirred at 90° C. overnight. The resulting mixture was quenched with IPA and water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and the solvent removed under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography using a gradient of 0-10% MeOH in EtOAc afforded the title compound;

Workup

  1. customThe resulting mixture was quenched with IPA and water
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe crude material was adsorbed onto silica and purification by chromatography

Sources & evidence

ORD record
ord-2239f6a0d8264994bb50318f74deebe3
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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