Acetic Acid → HCID 60684502, compound

HRID 606572Notes

Reaction equation

HRID 606572 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]=O.[CH3:9][O:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][NH:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]([O:10][CH3:9])=[O:19])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 12082Methyl 4-aminobenzoateHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 60684502HCID 60684502, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Methyl-2-imidazolecarboxaldehyde (5.0 mmol) and methyl-4-aminobenzoate (5.0 mmol) were mixed in MeOH (7 mL). Acetic acid (0.3 mL) was added and the mixture stirred for 30 minutes at room temperature. The reaction mixture was cooled, sodium cyanoborohydride (5.0 mmol) was added and the reaction allowed to stir at room temperature for a further 17 h. The reaction mixture was then concentrated under vacuum and partitioned between H2O and EtOAc. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with H2O, brine, dried over MgSO4 and the solvent removed under vacuum. The residue was purified by flash chromatography (silica gel, 5% MeOH in DCM) to give methyl 4-{[(1-methylimidazol-2-yl)methyl]amino}benzoate: m/z=246 in MS ES+ as a pale yellow solid which was used directly in the subsequent step.

Workup

  1. temperatureThe reaction mixture was cooled
  2. stirringto stir at room temperature for a further 17 h
  3. concentrationThe reaction mixture was then concentrated under vacuum
  4. custompartitioned between H2O and EtOAc
  5. extractionThe aqueous layer was extracted with EtOAc
  6. washthe combined organic layers were washed with H2O, brine
  7. dry with materialdried over MgSO4
  8. customthe solvent removed under vacuum
  9. customThe residue was purified by flash chromatography (silica gel, 5% MeOH in DCM)

Sources & evidence

ORD record
ord-6a73b10fffcd4c4bb757d84b4c8c003f
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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