Acetic Acid → N-[4-[(dipropylamino)methyl]phenyl]-4-[[(1-methylimidazol-2-yl)methyl-(1H-1,2,4-triazol-3-ylmethyl)amino]methyl]benzamide

HRID 1173998Notes

Reaction equation

HRID 1173998 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].[NH:33]1[CH:37]=[N:36][C:35]([CH:38]=O)=[N:34]1.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:1]([N:4]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:32])[C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH2:25][C:26]3[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=3)[CH2:38][C:35]3[N:36]=[CH:37][NH:33][N:34]=3)=[CH:19][CH:18]=2)=[CH:13][CH:14]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 66941901N-(4-dipropylaminomethyl-phenyl)-4-{[(1-methylimidazol-2-ylmethyl)-amino]methyl}benzamideHCID 1785199984H-1,2,4-triazole-3-carbaldehyde

Product 1

HCID 178457175N-[4-[(dipropylamino)methyl]phenyl]-4-[[(1-methylimidazol-2-yl)methyl-(1H-1,2,4-triazol-3-ylmethyl)amino]methyl]benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (256.8 mg) obtained in Example 122-4 was dissolved in methanol (7.7 ml) and added with 1H-[1,2,4]-triazol-3-carboxaldehyde (115.0 mg) and sodium cyanoborohydride (74.4 mg). Then, the solution was adjusted to pH 5 with acetic acid and stirred at room temperature for 14 hours. The reaction solution was concentrated under reduced pressure. Subsequently, the residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (337.9 mg) of the subject compound as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customSubsequently, the residue was purified through silica gel column chromatography (chloroform/methanol)
  3. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-f9d5ae11fca34a2a8089436daeb5b342
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

Loading…