HCID 68157734, compound → HCID 68158392, compound

HRID 243131Notes

Reaction equation

HRID 243131 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[F:26])[CH3:9])(C)(C)C>Cl.O1CCOCC1>[F:18][C:15]1[CH:16]=[CH:17][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:13]=2[CH:14]=1

Participants

4

Reactant 1

HCID 68157734HCID 68157734, compound

Product 1

HCID 68158392HCID 68158392, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

{(S)-1-[4-Fluoro-2-(2-fluorophenylamino)phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester (0.7 g, 1.80 mmol) was dissolved in 4M HCl in dioxane (10 mL) and the reaction mixture was heated to 70° C. for 5 h. The resultant mixture was concentrated in vacuo and the residue dissolved in DCM (40 mL) and washed with saturated aqueous NaHCO3 (20 mL) and brine (20 mL). The organic fraction was dried (MgSO4), filtered and concentrated in vacuo to afford a red gum. This was purified by column chromatography (silica gel, gradient 0-10% MeOH in DCM) to afford the title compound (0.22 g, 46%). LCMS (Method C): RT 1.74 min [M+H]+ 274.3

Workup

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in DCM (40 mL)
  3. washwashed with saturated aqueous NaHCO3 (20 mL) and brine (20 mL)
  4. dry with materialThe organic fraction was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a red gum
  8. customThis was purified by column chromatography (silica gel, gradient 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-e82f81124ec042fdbad7d11c2d039bf3
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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