Triethylamine → HCID 21868791, compound

HRID 1766426Notes

Reaction equation

HRID 1766426 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[C:10]([CH2:16][CH2:17][NH:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:11]([C:13](O)=[O:14])[N:12]=2)=[CH:4][CH:3]=1.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C>ClCCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[C:10]3[CH2:16][CH2:17][N:18]([CH:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[C:13](=[O:14])[C:11]=3[N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 181649HOAtHCID 21868795HCID 21868795, compound

Product 1

HCID 21868791HCID 21868791, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A mixture of 2-(4-chloro-phenyl)-1-(2-chloro-phenyl)-5-(2-cyclopentylamino-ethyl)-1H-imidazole-4-carboxylic acid I-5j (20 mg, 0.046 mmol), EDC (19 mg, 0.1 mmol), HOAt (13 mg, 0.1 mmol), and triethylamine (14 μl, 0.1 mmol) in 1,2-dichloroethane (20 ml) was stirred for 17 hours at room temperature. The reaction mixture was washed with sat'd aq NaHCO3 and the aqueous bicarbonate solution was back extracted once with CH2Cl2. The combined CH2Cl2 extracts were dried and concentrated in vacuo. The residue was dissolved in diethyl ether (1 ml) and several drops of 4M HCl in dioxane were added. The organic solution was decanted and additional ether was added. The mixture was stirred for several minutes and the solvent decanted again. The residue was dried under vacuum to give the desired produce 5A-1 as a colorless solid: +APCl MS (M+1) 426.3; 1H NMR (CDCl3): δ 7.62-7.57 (m, 1H), 7.53-7.47 (m, 1H), 7.44-7.39 (m, 1H), 7.37-7.33 (m, 2H), 7.32-7.28 (m, 1H), 7.24-7.19 (m, 2H), 5.16-5.06 (m, 1H), 3.56-3.50 (m, 2H) 3.2-3.17 (m, 2H), 2.71-2.56 (m, 2H), 1.92-1.83 (m, 2H), 1.76-1.46 (m, 4H).

Workup

  1. washThe reaction mixture was washed with sat'd aq NaHCO3
  2. extractionthe aqueous bicarbonate solution was back extracted once with CH2Cl2
  3. dry with materialThe combined CH2Cl2 extracts were dried
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in diethyl ether (1 ml)
  6. additionseveral drops of 4M HCl in dioxane were added
  7. customThe organic solution was decanted
  8. additionadditional ether was added
  9. stirringThe mixture was stirred for several minutes
  10. customthe solvent decanted again
  11. customThe residue was dried under vacuum
  12. customto give the
  13. customdesired produce 5A-1 as a colorless solid

Sources & evidence

ORD record
ord-6b8b6509b20140768bf3af3ac9b02923
Source dataset
uspto-grants-2007_06
Patent number
US07230024B2

Reaction notes

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