Triethylamine → HCID 86754324, compound

HRID 583410Notes

Reaction equation

HRID 583410 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[C:6]([N:8]([CH:10]([CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1)[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)[CH3:9])=[O:7].C(N(CC)CC)C.[Cl:43][C:44]1[CH:50]=[C:49]([CH3:51])[CH:48]=[CH:47][C:45]=1[NH2:46]>C(Cl)Cl.C(OCC)(=O)C>[Cl:43][C:44]1[CH:50]=[C:49]([CH3:51])[CH:48]=[CH:47][C:45]=1[NH:46][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH:10]([N:8]([C:6](=[O:7])[C:5]1[CH:4]=[C:3]([C:2]([F:35])([F:34])[F:1])[CH:29]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:27]=1)[CH3:9])[CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 120072-Chloro-p-toluidineHCID 21310531HCID 21310531, compound

Product 1

HCID 86754324HCID 86754324, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

160 mg (0.268 mmol) of 5-[N-(3,5-bistrifluoromethyl-benzoyl)-N-methyl-amino]-6-(1H-indol-3-yl)-hexanoic acid are dissolved in 10 ml of methylene chloride, and then 222 ml (1.34 mmol) of triethylamine, 48 ml (0.382 mmol) of 2-chloro-4-methyl-aniline and 271 ml of 50% propylphosphonic acid anhydride solution in ethyl acetate are added. The reaction mixture is stirred at room temperature for 20 hours, then washed twice with aqueous potassium carbonate solution. The aqueous phase is extracted twice with methylene chloride, and the organic phases are combined, dried over magnesium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/petroleum ether (first 1:2, then 3:1). The title compound is obtained in the form of white crystals. MS (EI): 352, 241, 222, 213, 130. TLC: ethyl acetate, Rf =0.59.

Workup

  1. washwashed twice with aqueous potassium carbonate solution
  2. extractionThe aqueous phase is extracted twice with methylene chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with ethyl acetate/petroleum ether (first 1:2

Sources & evidence

ORD record
ord-17a366bf80c44c75858004fc12225bf9
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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