Methanol → [(4-dipropylamino-butyl)-(4-{[(1-methoxycarbonylmethyl-1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-acetic acid methyl ester

HRID 2080840Notes

Reaction equation

HRID 2080840 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.C(N(CC)CC)C.Br[CH2:43][C:44]([O:46][CH3:47])=[O:45].C[OH:49].C1[CH2:54][O:53][CH2:52][CH2:51]1>>[CH3:47][O:46][C:44](=[O:45])[CH2:43][N:21]([CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:27][CH2:28][CH3:29])[CH2:30][CH2:31][CH3:32])[CH2:20][C:19]1[CH:33]=[CH:34][C:16]([CH2:15][N:7]([CH2:6][C:2]2[N:3]([CH2:51][C:52]([O:53][CH3:54])=[O:49])[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

Participants

6

Reactant 5

HCID 887MethanolHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 58801930CXCR4 antagonist 1

Product 1

HCID 67103883[(4-dipropylamino-butyl)-(4-{[(1-methoxycarbonylmethyl-1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-acetic acid methyl ester

Procedure

The compound (81.9 mg) obtained in Example 52-3 was dissolved in THF (2.0 ml) and added with triethylamine (76.0 μl) and methyl bromoacetate (46.0 μl) and the whole was stirred at room temperature for 11 hours under a nitrogen atmosphere. After completion of the reaction, the solution was added with methanol and the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (23.7 mg) as a yellow oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-711fdf2b5d4e4a9f941fab4121203091
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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