Sodium Carbonate → 2-Amino-5-(4-bromo-3-fluoro-phenyl)-5-(1-ethyl-5-methanesulfonyl-1H-pyrrol-3-yl)-3-methyl-3,5-dihydro-imidazol-4-one

HRID 2220473Notes

Reaction equation

HRID 2220473 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=O)[C:10]([C:12]2[CH:16]=[C:15]([S:17]([CH3:20])(=[O:19])=[O:18])[N:14]([CH2:21][CH3:22])[CH:13]=2)=O)C=[CH:6][C:7]=1[F:8].Cl.[CH3:25][NH:26][C:27]([NH2:29])=[NH:28].[C:30]([O-:33])([O-])=O.[Na+].[Na+]>O1CCOCC1.CCO>[NH2:29][C:27]1[N:26]([CH3:25])[C:30](=[O:33])[C:10]([C:9]2[CH:4]=[CH:3][C:2]([Br:1])=[C:7]([F:8])[CH:6]=2)([C:12]2[CH:16]=[C:15]([S:17]([CH3:20])(=[O:18])=[O:19])[N:14]([CH2:21][CH3:22])[CH:13]=2)[N:28]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 597726991-(3-Bromo-4-fluoro-phenyl)-2-(1-ethyl-5-methanesulfonyl-1H-pyrrol-3-yl)-ethane-1,2-dioneHCID 178485118HCID 178485118, compound

Product 1

HCID 686971262-Amino-5-(4-bromo-3-fluoro-phenyl)-5-(1-ethyl-5-methanesulfonyl-1H-pyrrol-3-yl)-3-methyl-3,5-dihydro-imidazol-4-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

A solution of 1-(3-bromo-4-fluoro-phenyl)-2-(1-ethyl-5-methanesulfonyl-1H-pyrrol-3-yl)-ethane-1,2-dione (0.32 g, 0.79 mmol) in dioxane and EtOH was treated with N-methylguanidine hydrochloride (0.17 g, 1.6 mmol) and Na2CO3(0.18 g, 1.66 mmol), heated to 105° C. for 18 h and concentrated in vacuo. The residue was dissolved in CHCl3, washed with H2O and brine, dried (Na2SO4) and evaporated to dryness at reduced pressure. Chromatography of this residue (silica gel, EtOAc and 1%-2% MeOH-EtOAc as eluent) yielded a solid; 1H NMR (400 MHz, CDCl3) δ: 1.44 (t, 3H, J=7.3 Hz), 3.08 (s, 3H), 3.10 (s, 3H), 3.97 (brs, 2H), 4.21 (q, 2H, J=7.3 Hz), 6.85 (d, 1H, J=2.1 Hz), 6.90 (d, 1H, J=2.1 Hz), 7.06 (t, 1H, J=8.5 Hz), 7.51 (m, 1H), 7.77 (dd, 1H, J=2.3, 6.6 Hz).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in CHCl3
  3. washwashed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness at reduced pressure
  6. customChromatography of this residue (silica gel, EtOAc and 1%-2% MeOH-EtOAc as eluent) yielded a solid

Sources & evidence

ORD record
ord-2f7c29dd0a334cea818e4a19c26e63c6
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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