Lawesson's reagent → HCID 59443510, compound

HRID 1927679Notes

Reaction equation

HRID 1927679 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[F:23][C:24]1[CH:25]=[C:26]([C:31](=O)[CH2:32][NH:33][C:34](=O)[CH2:35][CH2:36][C:37]2[N:38](S(N(C)C)(=O)=O)[CH:39]=[C:40]([CH2:42][C:43]([CH3:47])([CH3:46])[CH2:44][CH3:45])[N:41]=2)[CH:27]=[CH:28][C:29]=1[F:30]>C1(C)C=CC=CC=1>[F:23][C:24]1[CH:25]=[C:26]([C:31]2[S:10][C:34]([CH2:35][CH2:36][C:37]3[NH:41][C:40]([CH2:42][C:43]([CH3:47])([CH3:46])[CH2:44][CH3:45])=[CH:39][N:38]=3)=[N:33][CH:32]=2)[CH:27]=[CH:28][C:29]=1[F:30]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68673301HCID 68673301, compound

Product 1

HCID 59443510HCID 59443510, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Lawesson's reagent (50 mg, 0.12 mmol) was added to a solution of N-[2-(3,4-difluorophenyl)-2-oxoethyl]-3-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H -imidazol-2-yl]propanamide (30 mg, 0.06 mmol) in dry toluene (4 mL) at rt. After stirring at reflux for 30 min, volatiles were removed. The resulting residue was dissolved in THF (0.5 mL), and 2M aqueous hydrochloric acid (1.5 mL) was added. After stirring at 80° C. overnight, the volatiles were removed. The aqueous phase was diluted with water and washed with 1:5 ethyl acetate/diethyl ether. The aqueous phase was basified with 1N sodium hydroxide and extracted with ethyl acetate. Combined extracts were washed with brine, dried (sodium sulfate) and concentrated to afford the title compound, which was dissolved in methylene chloride and acidified with 1M hydrogen chloride in diethyl ether. Additional diethyl ether and hexane were added, and concentration afforded the HCl salt of the title compound. LC-MS: m/e 376 (M+H).

Workup

  1. temperatureat reflux for 30 min
  2. customvolatiles were removed
  3. dissolutionThe resulting residue was dissolved in THF (0.5 mL)
  4. addition2M aqueous hydrochloric acid (1.5 mL) was added
  5. stirringAfter stirring at 80° C. overnight
  6. customthe volatiles were removed
  7. additionThe aqueous phase was diluted with water
  8. washwashed with 1:5 ethyl acetate/diethyl ether
  9. extractionextracted with ethyl acetate
  10. washCombined extracts were washed with brine
  11. dry with materialdried (sodium sulfate)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-80b67b4eef9b41cd9427c11d6e97371d
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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