Formaldehyde → 5-dipropylamino-(2S)-[(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-methyl-amino]-pentanoic acid ethyl ester

HRID 2080890Notes

Reaction equation

HRID 2080890 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]([NH2:16])[CH2:6][CH2:7][CH2:8][N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])[CH3:2].[NH:18]1[CH:22]=CN=[C:19]1[CH2:23][N:24]([CH2:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1)[CH2:25][C:26]1[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=1.[C:41]([BH3-])#[N:42].[Na+].[CH2:45]=O>C(O)C.C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]([N:16]([CH2:37][C:36]1[CH:35]=[CH:34][C:33]([CH2:32][N:24]([CH2:23][C:19]2[NH:18][CH:22]=[CH:41][N:42]=2)[CH2:25][C:26]2[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=2)=[CH:40][CH:39]=1)[CH3:45])[CH2:6][CH2:7][CH2:8][N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])[CH3:2]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 866149184-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzaldehydeHCID 86614919(2S)-amino-5-dipropylamino-pentanoic acid ethyl ester

Product 1

HCID 116640015-dipropylamino-(2S)-[(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-methyl-amino]-pentanoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

The compound (54.2 mg) obtained in Example 92-3 and the compound (76.8 mg) obtained in Example 84-5 were dissolved in ethanol (4.3 ml) and added with acetic acid (80 μl). The solution was added with sodium cyanoborohydride (49.6 mg) and the whole was stirred at room temperature for 1.5 hours. The solution was added with a 36% formaldehyde aqueous solution (0.10 ml) and the whole was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off and the residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off and the residue was purified through silica gel column chromatography (chloroform), thereby obtaining the subject compound (94.9 mg) as a colorless oily substance.

Workup

  1. stirringthe whole was stirred at room temperature for 1 hour
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  6. extractionfollowed by extraction with chloroform
  7. washThe organic layer was washed with a saturated saline solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. distillationthe solvent was distilled off
  11. customthe residue was purified through silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-e194081f6cea4dc599d24f2c4ca628aa
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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