Formic Acid → (4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-formamide

HRID 2080839Notes

Reaction equation

HRID 2080839 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][NH:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:30][CH2:31][CH3:32])[CH2:27][CH2:28][CH3:29])=[CH:18][CH:17]=1)[CH2:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1.[CH:35](O)=[O:36].C(N)=O>C(O)C>[CH2:30]([N:26]([CH2:27][CH2:28][CH3:29])[CH2:25][CH2:24][CH2:23][CH2:22][N:21]([CH2:20][C:19]1[CH:33]=[CH:34][C:16]([CH2:15][N:7]([CH2:6][C:2]2[NH:3][CH:4]=[CH:5][N:1]=2)[CH2:8][C:9]2[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=2)=[CH:17][CH:18]=1)[CH:35]=[O:36])[CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 284Formic Acid2×HCID 713FormamideHCID 58801930CXCR4 antagonist 1

Product 1

HCID 11504167(4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-formamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

The compound (82.9 mg) obtained in Example 52-3 was dissolved in ethanol (1.0 ml) and added with formic acid (50 μl) and formamide (50 μl). The whole was stirred at an outside temperature of 10° C. for 3 hours. The solution was added with additional formic acid (60 μl) and the whole was stirred for 15 hours. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and added with a 1 mol/l sodium hydroxide aqueous solution to adjust the pH to 11. The aqueous layer was extracted with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining a hydrochloride (27.0 mg) of the subject compound as a yellow solid.

Workup

  1. stirringthe whole was stirred for 15 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in chloroform
  5. additionadded with a 1 mol/l sodium hydroxide aqueous solution
  6. extractionThe aqueous layer was extracted with chloroform
  7. washThe organic layer was washed with a saturated saline solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. customThe residue was purified through silica gel column chromatography (chloroform/methanol)
  11. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-138190fddb3f42f9a5f4789715df297a
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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