Potassium Carbonate → 5-(3,4-Difluorophenyl)-2,3-dihydro-4-methoxycarbonyl-1-(3-(4-methoxycarbonyl-4-phenylpiperidin-1-yl)prop-1-yl) aminocarbonyl-2(1H)-imidazolone

HRID 1003749Notes

Reaction equation

HRID 1003749 reaction equation
ClC(Cl)(Cl)[C:3]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([F:17])[CH:11]=2)=[C:8]([C:18]([O:20][CH3:21])=[O:19])[NH:7][C:6]1=[O:22])=[O:4].[NH2:25][CH2:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][C:32]([C:41]([O:43][CH3:44])=[O:42])([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[F:17][C:12]1[CH:11]=[C:10]([C:9]2[N:5]([C:3]([NH:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][C:32]([C:41]([O:43][CH3:44])=[O:42])([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH2:33][CH2:34]3)=[O:4])[C:6](=[O:22])[NH:7][C:8]=2[C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][C:13]=1[F:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 106838831-(3-Aminopropyl)-4-methoxycarbonyl-4-phenylpiperidineHCID 187982711-trichloroacetyl-5-(3,4-difluorophenyl)-2,3-dihydro-4-methoxycarbonyl-2(1H)-imidazolone

Product 1

HCID 187982775-(3,4-Difluorophenyl)-2,3-dihydro-4-methoxycarbonyl-1-(3-(4-methoxycarbonyl-4-phenylpiperidin-1-yl)prop-1-yl) aminocarbonyl-2(1H)-imidazoloneYield 2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-trichloroacetyl-5-(3,4-difluorophenyl)-2,3-dihydro-4-methoxycarbonyl-2(1H)-imidazolone (583 mg, 1.46 mmol), 1-(3-aminopropyl)-4-methoxycarbonyl-4-phenylpiperidine (808 mg, 2.92 mmol) and potassium carbonate (809 mg, 5.85 mmol) in dioxane (15 mL) was heated at reflux for 24 hours and then concentrated. The residue was partitioned between EtOAc and water. The organic layer was dried over Na2SO4, filtered and concentrated to give the crude product which was flash chromatographed over silica gel to give the product (15 mg, 2% yield). Hydrochloride salt: light brown solid; m.p. 134-136° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. concentrationconcentrated
  4. customThe residue was partitioned between EtOAc and water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product which
  9. customchromatographed over silica gel

Sources & evidence

ORD record
ord-9d49694ebe004365942cb81ef6ea5782
Source dataset
uspto-grants-2000_04
Patent number
US06046331

Reaction notes

Loading…