Sodium Hydroxide → HCID 178457176, compound

HRID 348716Notes

Reaction equation

HRID 348716 reaction equation
C(N(CCC)[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:27])[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:20][CH2:21][C:22]3[NH:23][CH:24]=[CH:25][N:26]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)CC.[NH:31]1[CH:35]=[N:34][C:33]([CH:36]=O)=[N:32]1.[C:38]([BH3-])#[N:39].[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH2:6]([N:39]([CH2:38][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:27])[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:20]([CH2:21][C:22]3[NH:26][CH:25]=[CH:24][N:23]=3)[CH2:36][C:33]3[N:34]=[CH:35][NH:31][N:32]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:7][CH2:8][CH3:9])[CH2:5][CH3:10]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 21084514N-[4-(dipropylamino)phenyl]-4-[(1H-imidazol-2-ylmethylamino)methyl]benzamideHCID 1785199984H-1,2,4-triazole-3-carbaldehyde

Product 1

HCID 178457176HCID 178457176, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The compound (100.0 mg) obtained in Example 47-3 was dissolved in methanol (3.0 ml). Then, the solution was added with 1H-[1,2,4]-triazol-3-carboxaldehyde (51.0 mg) synthesized by the method described in Heterocycles (vol. 15, No. 1, page 1981) and sodium cyanoborohydride (30.0 mg). Subsequently, the solution was adjusted to pH 5 with acetic acid and stirred at room temperature for 17 hours. After completion of the reaction, the reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and then subjected to separation/extraction with a mixture solution of chloroform/methanol. The organic layer was dried with anhydrous sodium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (37.4 mg) of the subject compound as a white solid.

Workup

  1. customsynthesized by the method
  2. customAfter completion of the reaction
  3. extractionsubjected to separation/extraction with a mixture solution of chloroform/methanol
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. distillationthe solvent was then distilled off
  6. customThe residue was purified through silica gel column chromatography (chloroform/methanol)
  7. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-af77e172aa1e4d5cb67c96c23aeac431
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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