HCID 68158136, compound → HCID 68157729, compound

HRID 243270Notes

Reaction equation

HRID 243270 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][C:9](=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][C:9]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12]2[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68158136HCID 68158136, compound

Product 1

HCID 68157729HCID 68157729, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

[(4-Fluoro-2-phenylaminophenylcarbamoyl)methyl]carbamic acid tert-butyl ester (0.37 g, 1.03 mmol) was taken up in AcOH (10 mL) and heated at 70° C. for 16 h. After cooling to RT, the volatiles were removed under reduced pressure, the resulting residue was partitioned between EtOAc and water and the mixture basified with Na2CO3. The organic layer was dried (Na2SO4) and concentrated in vacuo. The resulting oil was purified by column chromatography (Si—PCC, gradient 0-60% EtOAc in cyclohexane) to afford the title compound as a white foam (0.265 g, 75%). LCMS (Method B): RT 3.35 min [M+H]+ 342.03

Workup

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed under reduced pressure
  3. customthe resulting residue was partitioned between EtOAc and water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting oil was purified by column chromatography (Si—PCC, gradient 0-60% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-14bc08ea75a04e1d8f91d0a96b30ff64
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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