Diethyl Ether → HCID 59772735, compound

HRID 646249Notes

Reaction equation

HRID 646249 reaction equation
B(Br)(Br)Br.[NH2:5][C:6]1[N:10]([CH3:11])[C:9](=[O:12])[C:8]([C:21]2[CH:25]=[C:24]([C:26](=[O:29])[CH2:27][CH3:28])[N:23]([CH2:30][CH3:31])[CH:22]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=2)[N:7]=1.C(OCC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CO>[NH2:5][C:6]1[N:10]([CH3:11])[C:9](=[O:12])[C:8]([C:21]2[CH:25]=[C:24]([C:26](=[O:29])[CH2:27][CH3:28])[N:23]([CH2:30][CH3:31])[CH:22]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[N:7]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59264885HCID 59264885, compound

Product 1

HCID 59772735HCID 59772735, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1M in dichloromethane, 21 mL, 21.17 mmol) was added dropwise to a cold (−78° C.) suspension of 2-amino-5-(1-ethyl-5-propionyl-1-H-pyrrol-3-yl)-5-(3-methoxy-phenyl)-3-methyl-3,5-dihydro-imidazol-4-one (1.3 g, 3.52 mmol) in CH2Cl2. The mixture was allowed to warm to room temperature, stirred for 20 h, and poured slowly into cold (0° C.) ethyl ether, treated slowly with methanol over a 10 minute period, basified to pH 8 at 0° C. with saturated aqueous NaHCO3 and extracted with CHCl3. The combined CHCl3 extracts were washed with brine, dried over MgSO4 and evaporated to dryness. The resultant residue was purified by 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 (0.95 g, 72% yield), mp 101° C., 1H NMR (400 MHZ, DMSO-d6) δ 0.99 (t, 3H), 1.17 (t, 3H), 2.66-2.68 (q, 2H), 2.90 (s, 3H). 4.19-4.21 (q, 2H), 6.5 (bs, 2H), 6.55 (m, 1H), 6.84-6.88 (m, 3H), 7.01 (m, 2H), 9.21 (bs, 1H), MS m/e (M−H)− 353.1.

Workup

  1. extractionextracted with CHCl3
  2. washThe combined CHCl3 extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customThe resultant residue was purified by flash chromatography (ethyl acetate/methylene chloride/methyl alcohol/triethyl amine, 5/4.4/0.5/0.1)

Sources & evidence

ORD record
ord-d272bbc7f4284b92babb1d7f84c13630
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

Loading…