Triethylamine → HCID 178501048, compound

HRID 1797007Notes

Reaction equation

HRID 1797007 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)=O.[CH3:16][O:17][C:18]([C@H:20]1[CH2:25][CH2:24][C@H:23]([C:26](O)=O)[CH2:22][CH2:21]1)=[O:19].C([N:31](CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O.CC(O)=O>[CH3:16][O:17][C:18]([C@H:20]1[CH2:25][CH2:24][C@H:23]([C:26]2[NH:2][CH:3]=[C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=3)[N:31]=2)[CH2:22][CH2:21]1)=[O:19]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 133658852-Amino-1-(3-(trifluoromethyl)phenyl)ethan-1-one hydrochlorideHCID 178501163HCID 178501163, compound

Product 1

HCID 178501048HCID 178501048, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The solution of 2-amino-1-(3-trifluoromethyl-phenyl)-ethanone hydrochloride (50.2 mmol), trans-cyclohexane-1,4-dicarboxylic acid monomethyl ester (50.2 mmol), triethylamine (100.4 mmol) and BOP (50.2 mmol) in DMF (100 mL) was stirred overnight at room temperature. The mixture was diluted with water, extracted with EtOAc, washed with saturated NaHCO3 and brine, dried over Na2SO4, and concentrated under vacuum. The residue was triturated with ether and the precipitate was collected. The precipitate was mixed with NH4OAc (930 mmol) and 200 ml of AcOH and refluxed overnight. The excess AcOH was removed and purification by flash chromatography (95:5 CH2Cl2/MeOH) gave trans-4-[4-(3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-cyclohexyl-carboxylic acid methyl ester.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was triturated with ether
  6. customthe precipitate was collected
  7. temperaturerefluxed overnight
  8. customThe excess AcOH was removed
  9. custompurification by flash chromatography (95:5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-84b3799ec96d42c7be06cf1fee7b4be8
Source dataset
uspto-grants-2006_04
Patent number
US07034034B2

Reaction notes

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