Sodium Hydroxide → (4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-[4-(1-propylbutyl)-piperazin-1-yl]-methanone

HRID 348631Notes

Reaction equation

HRID 348631 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:22])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.[CH3:29][CH2:30][CH2:31][C:32](=O)[CH2:33][CH2:34][CH3:35].C([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C.C(N(CC)CC)C>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([N:23]2[CH2:24][CH2:25][N:26]([CH:32]([CH2:33][CH2:34][CH3:35])[CH2:31][CH2:30][CH3:29])[CH2:27][CH2:28]2)=[O:22])=[CH:19][CH:20]=1)[CH2:8][C:9]1[NH:13][CH:12]=[CH:11][N:10]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 312464-HeptanoneHCID 5003444Sodium cyanoborohydrideHCID 21084462(4-{[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-piperazin-1-yl-methanone

Product 1

HCID 10344979(4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-[4-(1-propylbutyl)-piperazin-1-yl]-methanone

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

The compound (57.7 mg) obtained in Example 32-2 was dissolved in methanol (1.73 ml) and then added with 4-heptanone (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (30.7 μl), sodium cyanoborohydride (13.8 mg), and triethylamine (76.5 μl). The solution was adjusted to pH 5 with acetic acid and stirred at room temperature for 7 days. The reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and then the whole was separated and extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (27.7 mg) of the subject compound as a pale-yellow solid.

Workup

  1. customthe whole was separated
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)
  6. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-43763437075e4d34b69e9473346ee79c
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

Loading…