2-(4-Fluorophenyl)acetic acid → HCID 15512772, compound

HRID 991938Notes

Reaction equation

HRID 991938 reaction equation
[N:1]1([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2C2N=C(N)C=CC=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=O)=[CH:25][CH:24]=1.C([N:35]=[C:36]=[N:37][CH2:38][CH2:39][CH2:40]N(C)C)C.[CH:44](N(C(C)C)CC)(C)C>O.CN(C)C=O>[NH2:35][C:36]1[N:37]=[C:38]([C:12]2[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][N:1]3[CH2:2][CH2:3][N:4]([C:30](=[O:32])[CH2:29][C:26]4[CH:25]=[CH:24][C:23]([F:22])=[CH:28][CH:27]=4)[CH2:5][CH2:6]3)=[CH:14][CH:13]=2)[CH:39]=[CH:40][CH:44]=1

Participants

7

Reactant 4

HCID 98372-(4-Fluorophenyl)acetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 18414425HCID 18414425, compound

Product 1

HCID 15512772HCID 15512772, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a 50 mL round-bottomed flask equipped with nitrogen inlet were added 200 mg (0.71 mmol) 6-((2-(piperazin-1-yl)ethyl)phenyl)-pyridin-2-ylamine,10 mL dry dimethyformamide, 109 mg (0.71 mmol) 4-fluorophenylacetic acid, 204 mg (1.1 mmol) ethyl(3-dimethylaminopropyl)carbodiimide, and 0.36 mL (2.1 mmol) diisopropylethylamine. The reaction was stirred at room temperature for 18 hours, poured into water and extracted into ethyl acetate. The organic layer was extracted into 1 N hydrochloric acid, the aqueous layer washed with fresh ethyl acetate, and the aqueous layer basified with 1 N aqueous sodium hydroxide solution and extracted into ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using 3% methanol in methylene chloride to afford 100 mg (34%) of the product as a tan solid, mp 143-145° C.

Workup

  1. customTo a 50 mL round-bottomed flask equipped with nitrogen inlet
  2. extractionextracted into ethyl acetate
  3. extractionThe organic layer was extracted into 1 N hydrochloric acid
  4. washthe aqueous layer washed with fresh ethyl acetate
  5. extractionextracted into ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue was chromatographed on silica gel using 3% methanol in methylene chloride

Sources & evidence

ORD record
ord-b92f1803de3940c58bfe4ac9aa8fe33c
Source dataset
uspto-grants-2002_10
Patent number
US06465491B2

Reaction notes

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