3-Pyridinecarboxaldehyde → HCID 9983833, compound

HRID 1173906Notes

Reaction equation

HRID 1173906 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.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=O)[CH:32]=1.[C:39]([BH3-])#[N:40].[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[CH2:6]([N:40]([CH2:39][C:5]1[CH:6]=[CH:7][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:23][CH:24]=[CH:25][N:26]=3)[CH2:37][C:33]3[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=3)=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:7][CH2:8][CH3:9])[CH2:5][CH3:10]

Participants

7

Reactant 4

HCID 103713-PyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 21084514N-[4-(dipropylamino)phenyl]-4-[(1H-imidazol-2-ylmethylamino)methyl]benzamide

Product 1

HCID 9983833HCID 9983833, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The compound (100 mg) obtained in Example 47-3 was dissolved in methanol (5.0 ml) and added with pyridin-3-aldehyde (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (44.8 μl), followed by the addition of sodium cyanoborohydride (44.9 mg). Then, the reaction solution was adjusted to about pH 5 with acetic acid, followed by stirring at room temperature for 65 hours. The reaction solution was added with a saturated aqueous sodium bicarbonate solution and then extracted with chloroform. The organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off. The resulting crude product was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (95.8 mg) of the subject compound as a white solid.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationSubsequently, the solvent was distilled off
  5. customThe resulting crude product was purified through silica gel column chromatography (chloroform/methanol)
  6. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-d481ba6f09c6446e80a45c0ac57f1929
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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