Acetic Acid → 4-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethyl-phenyl)-benzamide

HRID 2080760Notes

Reaction equation

HRID 2080760 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:32])[C:17]2[CH:22]=[CH:21][C:20]([CH2:23][NH:24][CH2:25][C:26]3[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=3)=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].C([BH3-])#N.[Na+].C(O)(=O)C.[CH3:41][C:42]1[C:43]([CH:49]=O)=[N:44][CH:45]=[C:46]([CH3:48])[CH:47]=1>CO>[CH3:41][C:42]1[C:43]([CH2:49][N:24]([CH2:23][C:20]2[CH:21]=[CH:22][C:17]([C:16]([NH:15][C:12]3[CH:11]=[CH:10][C:9]([CH2:8][N:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])=[CH:14][CH:13]=3)=[O:32])=[CH:18][CH:19]=2)[CH2:25][C:26]2[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=2)=[N:44][CH:45]=[C:46]([CH3:48])[CH:47]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 187316833,5-Dimethylpyridine-2-carbaldehydeHCID 66941901N-(4-dipropylaminomethyl-phenyl)-4-{[(1-methylimidazol-2-ylmethyl)-amino]methyl}benzamide

Product 1

HCID 117066654-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethyl-phenyl)-benzamideYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (155 mg) obtained in Example 15-5 was dissolved in anhydrous methanol (3.0 ml) and added with sodium cyanoborohydride (33.7 mg), acetic acid (0.50 ml), and the compound (58.0 mg) obtained in Example 15-6, and the whole was stirred at room temperature for 2 days under a nitrogen atmosphere. After completion of the reaction, the solvent was distilled off. The resultant was dissolved in chloroform and added with a 1 mol/l sodium hydroxide aqueous solution, followed by stirring for a while. Then, the solution was subjected to extraction with chloroform and washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution. The organic layer was dried with anhydrous sodium 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 (174 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe resultant was dissolved in chloroform
  4. additionadded with a 1 mol/l sodium hydroxide aqueous solution
  5. extractionThen, the solution was subjected to extraction with chloroform
  6. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. distillationthe solvent was distilled off
  9. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  10. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-3e7b1cb902564f24bf099b15134320e8
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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