Sodium Hydroxide → HCID 49771573, compound

HRID 348692Notes

Reaction equation

HRID 348692 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.[CH2:31]([N:34]1[CH:38]=[CH:37][N:36]=[C:35]1[CH:39]=O)[CH2:32][CH3:33].[C:41]([BH3-])#[N:42].[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH2:6]([N:42]([CH2:41][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:27])[C:13]2[CH:14]=[CH:15][C:16]([CH2:19][N:20]([CH2:21][C:22]3[NH:26][CH:25]=[CH:24][N:23]=3)[CH2:39][C:35]3[N:34]([CH2:31][CH2:32][CH3:33])[CH:38]=[CH:37][N:36]=3)=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)[CH2:7][CH2:8][CH3:9])[CH2:5][CH3:10]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 47776601-Propyl-1H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21084514N-[4-(dipropylamino)phenyl]-4-[(1H-imidazol-2-ylmethylamino)methyl]benzamide

Product 1

HCID 49771573HCID 49771573, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The compound (120 mg) obtained in Example 47-3 was dissolved in methanol (5.0 ml) and then added with the compound (57.0 mg) obtained in Example 91-1 and sodium cyanoborohydride (18.0 mg). Then, the solution was adjusted to pH 5 with acetic acid and then stirred at room temperature for 2 days. After completion of the reaction, a 1 mol/l sodium hydroxide aqueous solution was added to the reaction solution, followed by separation/extraction with chloroform. 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 then treated with hydrochloric acid, thereby obtaining hydrochloride (201 mg) of the subject compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-cb51373f26b04f4ab7170e08db83c49d
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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