Cesium carbonate → HCID 15950255, compound

HRID 2220468Notes

Reaction equation

HRID 2220468 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:16]2[CH:20]=[C:19]([C:21](=[O:24])[CH2:22][CH3:23])[N:18]([CH2:25][CH3:26])[CH:17]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].I[CH2:34][CH2:35][CH3:36]>CN(C=O)C>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:16]2[CH:20]=[C:19]([C:21](=[O:24])[CH2:22][CH3:23])[N:18]([CH2:25][CH3:26])[CH:17]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:34][CH2:35][CH3:36])[CH:10]=2)[N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 336431-IodopropaneHCID 59772735HCID 59772735, compound

Product 1

HCID 15950255HCID 15950255, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, a solution of 2-amino-5-(1-ethyl-5-propionyl-1-H-pyrrol-3-yl)-5-(3-hydroxy-phenyl)-3-methyl-3,5-dihydro-imidazol-4-one (0.08 g, 0.225 mmol) in DMF (5 mL) was treated with Cs2CO3 (0.15 g, 0.45 mmol) and iodopropane (0.046 g, 0.27 mmol). The reaction mixture was sealed and stirred at room temperature for 20 hours. The solvent was removed in vacuo and the residue was dissolved in CHCl3 and filtered. The filtrate was evaporated. The resultant residue was purified by combi flash chromatography (ethyl acetate/methylene chloride/methyl alcohol/triethyl amine, 5/4.4/0.5/0.1) to give the title compound as a white solid (0.04 g, 45% yield), mp 95° C., 1H NMR (400 MHZ, DMSO-d6) δ 0.89-0.99 (dt, 6H), 1.15 (t, 3H), 1.64-1.66 (m, 2H), 2.64-2.68 (m, 2H), 2.9 (s, 3H), 3.81 (m, 2H), 4.20 (m, 2H), 6.50 (bs, 2H), 6.72-6.74 (m, 1H), 6.87 (s, 1H), 7.0-7.02 (m, 3H), 7.14 (m, 1H), MS m/e (M+H)+ 397.

Workup

  1. customThe reaction mixture was sealed
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in CHCl3
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customThe resultant residue was purified by combi flash chromatography (ethyl acetate/methylene chloride/methyl alcohol/triethyl amine, 5/4.4/0.5/0.1)

Sources & evidence

ORD record
ord-662a8f0de9b9462f88d5437e2bb062d7
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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