Dimethylformamide → HCID 66955181, compound

HRID 2088455Notes

Reaction equation

HRID 2088455 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[C:12]([C:14](=O)[CH3:15])[C:11]([F:17])=[CH:10][C:9]=1[CH3:18])([CH3:4])([CH3:3])[CH3:2].CO[C:22]([N:26](C)C)(OC)[CH3:23].C[N:30](C=O)C>>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[C:12]([C:14]2[CH:15]=[C:22]([CH3:23])[NH:26][N:30]=2)[C:11]([F:17])=[CH:10][C:9]=1[CH3:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 66955288HCID 66955288, compound

Product 1

HCID 66955181HCID 66955181, compound

Procedure

A solution of (5-Acetyl-4-fluoro-2-methyl-phenyl)-carbamic acid tert-butyl ester (425 mg) and (1,1-dimethoxy-ethyl)-dimethyl-amine (653 mg) in DMF (2 ml) was heated at 90° C. for 3 hours, then cooled to room temperature. Solvent was removed under reduced pressure, and the residue was dissolved in a mixture of EtOH (25 ml) and THF (5 ml). The mixture was cooled to 0° C., and hydrazine hydrate (5 ml) at 0° C. was added. The mixture was stirred for 16 hours at room temperature, then concentrated under reduced pressure. The residue was purified by“flash chromatography” (0 to 30% EtOAc in hexanes) to give 370 mg of [4-fluoro-2-methyl-5-(5-methyl-1H-pyrazol-3-yl)-phenyl]-carbamic acid tert-butyl ester.

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of EtOH (25 ml) and THF (5 ml)
  3. temperatureThe mixture was cooled to 0° C.
  4. additionhydrazine hydrate (5 ml) at 0° C. was added
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by“flash chromatography” (0 to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ff1773ea9ef6467ba74dcde9ff6787ee
Source dataset
uspto-grants-2013_05
Patent number
US08435990B2

Reaction notes

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