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Acetic Acid → N-(4-dipropylamino-butyl)-4-{[(1-methyl-1H-imidazol-2-ylmethyl)-(5-methyl-pyridin-2-ylmethyl)-amino]-methyl}-benzamide

HRID 2080778
Notes
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Reaction equation

HRID 2080778 reaction equation
[CH2:1]([N:4]([CH2:27][CH2:28][CH3:29])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:26])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][NH:18][CH2:19][C:20]2[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=2)=[CH:13][CH:12]=1)[CH2:2][CH3:3].C([BH3-])#N.[Na+].C(O)(=O)C.[CH3:38][C:39]1[CH:40]=[CH:41][C:42]([CH:45]=O)=[N:43][CH:44]=1>CO.O>[CH2:27]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:26])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]([CH2:19][C:20]2[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=2)[CH2:45][C:42]2[CH:41]=[CH:40][C:39]([CH3:38])=[CH:44][N:43]=2)=[CH:13][CH:12]=1)[CH2:28][CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 104643395-Methylpyridine-2-carbaldehydeHCID 67103805N-(4-dipropylamino-butyl)-4-{[(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzamide

Product 1

HCID 11627535N-(4-dipropylamino-butyl)-4-{[(1-methyl-1H-imidazol-2-ylmethyl)-(5-methyl-pyridin-2-ylmethyl)-amino]-methyl}-benzamide
Yield 32%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

The compound (782 mg) obtained in Example 20-3 was dissolved in anhydrous methanol (12 ml) and then added with sodium cyanoborohydride (380 mg) and acetic acid (1.5 ml). Then, the solution was added with a methanol solution (2.0 ml) containing the compound (289 mg) obtained in Example 20-4 at −10° C. and then stirred at room temperature for 12 hours under a nitrogen atmosphere. After completion of the reaction, water was added thereto to stop the reaction. The solvent was distilled off under reduced pressure and chloroform and a 1 mol/l sodium hydroxide aqueous solution were added to the residue to make the pH of the aqueous layer about 10, followed by extraction of the aqueous layer with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. The resultant was then concentrated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and then treated with hydrochloric acid, thereby obtaining a hydrochloride (316 mg) of the subject compound as a white solid.

Workup

  1. additionwas added
  2. customthe reaction
  3. distillationThe solvent was distilled off under reduced pressure and chloroform
  4. additiona 1 mol/l sodium hydroxide aqueous solution were added to the residue
  5. extractionfollowed by extraction of the aqueous layer with chloroform
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationThe resultant was then concentrated under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  10. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-e861a9e05765410ab1998cc8459ea621
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932281B2

Reaction notes

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