Hydrochloric Acid → 6-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide

HRID 724210Notes

Reaction equation

HRID 724210 reaction equation
O[C:2]1([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([C:20]([NH:22][CH3:23])=[O:21])[CH:14]=[CH:13]3)[C:9]2[N:5]([CH:6]=[N:7][CH:8]=2)[CH2:4][CH2:3]1.Cl.[H][H]>CO.[C].[Pd]>[CH:8]1[N:7]=[CH:6][N:5]2[CH2:4][CH2:3][CH:2]([C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[CH:16]=[C:15]([C:20]([NH:22][CH3:23])=[O:21])[CH:14]=[CH:13]4)[C:9]=12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 98830296-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamideHCID 178418361HCID 178418361, compound

Product 1

HCID 218796206-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamideYield 72.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide (77 mg) was dissolved in methanol (5 ml). 1 N Hydrochloric acid (0.5 ml) and 10% palladium carbon (50% wet, 39 mg) were added, and the mixture was vigorously stirred for 12 h under 4 kg/cm2 hydrogen atmosphere. The catalyst was filtered off and the residue was washed with methanol. The filtrate and the washing were combined and aqueous potassium carbonate solution (0.25 M; 1 ml) was added. After neutralization, the solvent was evaporated under reduced pressure, and the residue was purified by flash silica gel column chromatography (eluent, chloroform/methanol containing ammonia (7%); 19/1). The eluate was recrystallized from chloroform-ether to give the title compound (53 mg) as colorless crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. washthe residue was washed with methanol
  3. additionaqueous potassium carbonate solution (0.25 M; 1 ml) was added
  4. customAfter neutralization, the solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash silica gel column chromatography (eluent, chloroform/methanol containing ammonia (7%); 19/1)
  6. customThe eluate was recrystallized from chloroform-ether

Sources & evidence

ORD record
ord-cc9348aa939140dba8294ace74a5f4a0
Source dataset
uspto-grants-2006_11
Patent number
US07141598B2

Reaction notes

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