Hydrochloric Acid → HCID 57683230, compound

HRID 494381Notes

Reaction equation

HRID 494381 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)[CH3:2].C(N(CC)CC)C.[F:21][C:22]([F:39])([F:38])[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[C:30]([C:35](Cl)=[O:36])=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:25][CH:24]=1.Cl>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:35]([C:30]2[C:29]([C:26]3[CH:27]=[CH:28][C:23]([C:22]([F:21])([F:38])[F:39])=[CH:24][CH:25]=3)=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:36])=[CH:10][CH:11]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 225219p-Aminophenylacetic acid ethyl esterHCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chloride

Product 1

HCID 57683230HCID 57683230, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-aminophenylacetic acid ethyl ester (3.41 g), triethylamine (3.2 mL) and methylene chloride (30 mL) was added dropwise a solution of the 4′-trifluoromethylbiphenyl-2-carboxylic acid chloride (5.40 g) obtained in Example 1-d) in methylene chloride (10 mL) under ice-cooling, and the mixture was stirred at room temperature overnight. After addition of 1N hydrochloric acid, the reaction mixture was diluted with ethyl acetate, and the organic layer was washed with saturated brine, saturated aqueous sodium bicarbonate and saturated brine, dried over sodium sulfate, and then concentrated to give the title compound (8.12 g).

Workup

  1. temperaturecooling
  2. washthe organic layer was washed with saturated brine, saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-64067b9301994b54ba7c144e22240127
Source dataset
uspto-grants-2009_05
Patent number
US07538140B2

Reaction notes

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