Water → HCID 58948136, compound

HRID 639600Notes

Reaction equation

HRID 639600 reaction equation
C(OC(=O)[N:7]([CH2:12][CH2:13][C:14]1[N:19]=[C:18]([NH:20]CC2C=CC=CC=2)[C:17]2[NH:28][C:29](=[O:38])[N:30]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:16]=2[CH:15]=1)[CH2:8][CH2:9][O:10][CH3:11])(C)(C)C.O.C([O-])(O)=O.[Na+]>S(=O)(=O)(O)O>[NH2:20][C:18]1[C:17]2[NH:28][C:29](=[O:38])[N:30]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:16]=2[CH:15]=[C:14]([CH2:13][CH2:12][NH:7][CH2:8][CH2:9][O:10][CH3:11])[N:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 86614464HCID 86614464, compound

Product 1

HCID 58948136HCID 58948136, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

[2-(1-Benzyl-4-benzylamino-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]pyridine-6-yl)-ethyl]-(2-methoxy-ethyl)-carbamic acid tert-butyl ester (64 mg, 0.12 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, 98:2 with increasing gradient to DCM:MeOH:NH3 90:10:1 to afford the title compound as a yellow solid, (4.2 mg, 11%).

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, 98:2 with increasing gradient to DCM:MeOH:NH3 90:10:1

Sources & evidence

ORD record
ord-f08c1eaa259a4a10a27a82e40495f62c
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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