Tetrahydrofuran → HCID 69210344, compound

HRID 30725Notes

Reaction equation

HRID 30725 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([OH:18])=O)=[CH:4][CH:3]=1.[C:19](Cl)(=[O:23])[C:20](Cl)=O.[O:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:11][C:10]2[CH:9]=[CH:8][C:28]([C:29]([O:23][CH2:19][CH3:20])=[O:25])=[CH:27][CH:26]=2)=[O:18])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 69208981(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylic acid

Product 1

HCID 69210344HCID 69210344, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylic acid (600 mg), oxalyl chloride (260 μL), tetrahydrofuran (10 mL) and N,N-dimethylformamide (2 drops) was stirred at room temperature for 3 hrs. The reaction mixture was concentrated and diluted with N,N-dimethylacetamide (10 mL). Ethyl 4-aminobenzoate (482 mg) was added and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was poured into a 0.1N aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate, and then with saturated brine, dried (MgSO4) and concentrated. The obtained solid was recrystallized from acetone-hexane to give ethyl 4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl}amino)benzoate (810 mg, yield 84%) as colorless needle crystals. melting point: 202-203° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with N,N-dimethylacetamide (10 mL)
  3. additionEthyl 4-aminobenzoate (482 mg) was added
  4. stirringthe mixture was stirred at room temperature for 3 hrs
  5. additionThe reaction mixture was poured into a 0.1N aqueous hydrochloric acid solution
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate
  8. dry with materialwith saturated brine, dried (MgSO4)
  9. concentrationconcentrated
  10. customThe obtained solid was recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-93f08d1928584bddb8189923ab186b98
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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