Water → HCID 58948144, compound

HRID 639599Notes

Reaction equation

HRID 639599 reaction equation
[CH2:1]([N:8]1[C:16]2[CH:15]=[C:14]([CH2:17][CH2:18][O:19][CH3:20])[N:13]=[C:12]([NH:21]CC3C=CC=CC=3)[C:11]=2[NH:10][C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C([O-])(O)=O.[Na+]>S(=O)(=O)(O)O>[NH2:21][C:12]1[C:11]2[NH:10][C:9](=[O:29])[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:16]=2[CH:15]=[C:14]([CH2:17][CH2:18][O:19][CH3:20])[N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 67456724HCID 67456724, compound

Product 1

HCID 58948144HCID 58948144, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

1-Benzyl-4-benzylamino-6-(2-methoxy-ethyl)-1,3-dihydro-imidazo[4,5-c]pyridine-2-one (32 mg, 0.082 mmol) was stirred in concentrated sulphuric acid (2 ml) for 30 minutes. Water (5 ml) was added and the mixture added drop-wise to a stirred solution of saturated NaHCO3 to achieve a basic pH. The aqueous was extracted with 2×EtOAc and the combined organics dried and concentrated to afford a yellow solid. The mixture of isomers was separated by column chromatography on silica, eluting with DCM:MeOH, 97:3 with increasing gradient to DCM:MeOH:NH3 95:5:0.5 to afford the title compound as a pale yellow solid, (3.1 mg, 13%)

Workup

  1. extractionThe aqueous was extracted with 2×EtOAc
  2. customthe combined organics dried
  3. concentrationconcentrated
  4. customto afford a yellow solid
  5. additionThe mixture of isomers
  6. customwas separated by column chromatography on silica
  7. washeluting with DCM
  8. temperatureMeOH, 97:3 with increasing gradient to DCM:MeOH:NH3 95:5:0.5

Sources & evidence

ORD record
ord-63db447db8af476b86d9599a0bd37a06
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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