Triethylamine → N-Methoxy-N-methyl-1-(2-naphthylmethyl)-1H-imidazol-5-ylacetamide

HRID 267082

Reaction equation

HRID 267082 reaction equation
Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][N:13]1[C:17]([CH2:18][C:19]([OH:21])=O)=[CH:16][N:15]=[CH:14]1.[OH:22][N:23]1[C:28](=O)C2C=CC=CC=2N=N1.Cl.[CH3:35]N(C)CCCN=C=NCC.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[CH3:35][O:22][N:23]([CH3:28])[C:19](=[O:21])[CH2:18][C:17]1[N:13]([CH2:12][C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:2]=2)[CH:14]=[N:15][CH:16]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 702062051-(2-naphthylmethyl)-1H-imidazol-5-ylacetic acid hydrochloride

Product 1

HCID 86751125N-Methoxy-N-methyl-1-(2-naphthylmethyl)-1H-imidazol-5-ylacetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-naphthylmethyl)-1H-imidazol-5-ylacetic acid hydrochloride (prepared in Example 4, 0.819 mg, 2.70 mmol) in dimethylformamide (15 ml) was added sequentially N, O-dimethylhydroxylamine hydrochloride (293 mg, 3.0 mmol), 3-hydroxy-1,2,3-benzotriazin-4(3H)-one (HOOBT, 489 mg, 3.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 575 mg, 3.0 mmol) and triethylamine (1.67 ml, 12.0 mmol) and the resulting mixture stirred at room temperature for 18 h. Saturated aq. sodium bicarbonate (30 ml) and water (30 ml) were added and the mixture was extracted with methylene chloride (2×50 ml). The combined organic extracts were washed with brine (50 ml) and the solvent evaporated in vacuo. The residue was purified by flash chromatography (2-4% methanol/methylene chloride gradient elution) to provide the title compound as an oil.

Workup

  1. extractionthe mixture was extracted with methylene chloride (2×50 ml)
  2. washThe combined organic extracts were washed with brine (50 ml)
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by flash chromatography (2-4% methanol/methylene chloride gradient elution)

Sources & evidence

ORD record
ord-b1467f2bd5694d53a51470721eae605e
Source dataset
uspto-grants-1997_07
Patent number
US05652257

Linked notes

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