Sodium Hydroxide → HCID 11533761, compound

HRID 2080854Notes

Reaction equation

HRID 2080854 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][N:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=1)[CH2:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13].[NH:27]1[CH:31]=[CH:30][N:29]=[C:28]1[CH:32]=O.[C:34]([BH3-])#[N:35].[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:26])[CH2:4][N:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH2:3][C:4]2[NH:5][CH:6]=[CH:34][N:35]=2)[CH2:32][C:28]2[NH:29][CH:30]=[CH:31][N:27]=2)=[CH:20][CH:19]=1)[CH2:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 249551H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67103855HCID 67103855, compound

Product 1

HCID 11533761HCID 11533761, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The compound (1.4928 g) obtained in Example 64-1 was dissolved in anhydrous methanol (59.6 ml) and added with 2-imidazole carboxaldehyde (1.1848 g) and sodium cyanoborohydride (1.0331 g). After the solution was adjusted to pH 5 with acetic acid, the whole was stirred at room temperature for 3 days. After completion of the reaction, the resultant was added with a 1 mol/l sodium hydroxide aqueous solution and the whole was subjected to extraction with chloroform. The resultant was dried with magnesium sulfate and the solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining a hydrochloride (705.7 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. extractionthe whole was subjected to extraction with chloroform
  3. dry with materialThe resultant was dried with magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  6. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-b8d31d18dbaf46c1a81e0eab4a5615b7
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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