Triethylamine → HCID 11620129, compound

HRID 2080838Notes

Reaction equation

HRID 2080838 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.[CH2:35]([N:37](CC)CC)C.C(Br)#N.C(=O)([O-])O.[Na+]>C1COCC1>[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)[C:35]#[N:37])[CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 58801930CXCR4 antagonist 1

Product 1

HCID 11620129HCID 11620129, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (13.4 mg) obtained in Example 52-3 was dissolved in THF (0.26 ml) and added with triethylamine (10 μl) and bromocyan (3.65 mg) and the whole was stirred at room temperature for 2 hours under a nitrogen atmosphere. After completion of the reaction, the solution was added with a saturated aqueous sodium hydrogen carbonate solution to neutralize the solution and the solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/methanol) and treated with tartaric acid, thereby obtaining a tartrate (12.5 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. customThe residue was purified through silica gel column chromatography (chloroform/methanol)
  4. additiontreated with tartaric acid

Sources & evidence

ORD record
ord-62053a8517c14d8389513fe688e18e22
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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