Cesium carbonate → HCID 59772784, compound

HRID 646251Notes

Reaction equation

HRID 646251 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[CH:19]=2)([C:9]2[CH:13]=[C:12]([C:14](=[O:17])[CH2:15][CH3:16])[NH:11][CH:10]=2)[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].I[CH2:32][CH2:33][CH3:34]>CN(C=O)C>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[CH:19]=2)([C:9]2[CH:13]=[C:12]([C:14](=[O:17])[CH2:15][CH3:16])[N:11]([CH2:32][CH2:33][CH3:34])[CH:10]=2)[N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 336431-IodopropaneHCID 59772698HCID 59772698, compound

Product 1

HCID 59772784HCID 59772784, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, to a solution of 2-amino-5-(3-bromo-phenyl)-3-methyl-5-(5-propionyl-1H-pyrrol-3-yl)-3,5-dihydro-imidazol-4-one (0.2 g, 0.51 mmol) in DMF (5 mL) was added Cs2CO3 (0.33 g, 1.02 mmol) and iodopropane (0.12 g, 0.70 mmol). The reaction mixture was sealed and stirred at room temperature for 20 hours. DMF was removed in vacuo, the residue was taken back CHCl3 and filtered. Evaporation and purification by combi flash chromatography (methylene chloride/methyl alcohol/triethyl amine, 9.5/0.4/0.1) gave the title compound as a white solid (0.16 g, 72% yield), mp 260° C., 1H NMR (400 MHZ, CDCl3) δ 0.73 (t, 3H), 1.01 (t, 3H), 1.03 (q, 2H), 2.66 (m, 2H), 2.91 (s, 3H), 4.12 (q, 2H), 6.6 (bs, 2H), 6.87 (s, 1H), 6.98 (s, 1H), 7.23 (m, 1H), 7.37 (m, 1H), 7.45 (m, 1H), 7.57 (m, 1H), MS m/e (M−H)− 429.1.

Workup

  1. customThe reaction mixture was sealed
  2. customDMF was removed in vacuo
  3. filtrationfiltered
  4. customEvaporation and purification by combi flash chromatography (methylene chloride/methyl alcohol/triethyl amine, 9.5/0.4/0.1)

Sources & evidence

ORD record
ord-1adc649287a0479b9f6b7904c2079ee9
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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