Methanol → 4-{[bis(1H-imidazol-2-ylmethyl)amino]methyl)naphthalene-1-carboxylic acid methyl ester

HRID 348628Notes

Reaction equation

HRID 348628 reaction equation
C[C:2]1[CH:11]=[C:10]([CH2:12][NH2:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:14]([OH:16])=O.[CH3:17][OH:18].[NH:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH:24]=O.[C:26]([BH3-])#[N:27].[Na+]>C(O)(=O)C>[CH3:17][O:18][C:14]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([CH2:12][N:13]([CH2:24][C:20]2[NH:19][CH:23]=[CH:26][N:27]=2)[CH2:24][C:20]2[NH:21][CH:22]=[CH:23][N:19]=2)=[CH:11][CH:2]=1)=[O:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 249551H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23079313methyl-4-aminomethyl-1-naphthalene Carboxylic Acid

Product 1

HCID 669413384-{[bis(1H-imidazol-2-ylmethyl)amino]methyl)naphthalene-1-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The compound (390 mg) obtained in Example 36-2 was dissolved by the addition of anhydrous methanol (20 ml), and the solution was added with imidazole-2-carboxaldehyde (453 mg) and sodium cyanoborohydride (341 mg), and adjusted to pH 5 by the addition of acetic acid (0.5 ml), followed by stirring for 18 hours. After completion of the reaction, the methanol was distilled off and the residue was then added with 1 mol/l sodium hydroxide (20 ml), followed by extraction with chloroform. The organic layer was washed with saturated saline solution and then dried with anhydrous magnesium sulfate. After that, the solvent was distilled off and the residue was then dried, thereby obtaining the subject compound (680 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe methanol was distilled off
  3. additionthe residue was then added with 1 mol/l sodium hydroxide (20 ml)
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with saturated saline solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. distillationAfter that, the solvent was distilled off
  8. customthe residue was then dried

Sources & evidence

ORD record
ord-657f382f15d94298bcee57d6bb12ab7f
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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