Oxalyl chloride → HCID 9880843, compound

HRID 352419Notes

Reaction equation

HRID 352419 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=O)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[NH:24]1[C:28]2[CH2:29][CH2:30][CH2:31][C:27]=2[C:26]([NH2:32])=[N:25]1>O1CCCC1.CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C:15]([NH:32][C:26]3[C:27]4[CH2:31][CH2:30][CH2:29][C:28]=4[NH:24][N:25]=3)=[O:17])=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 1393660(3'-Fluoro[1,1'-biphenyl]-4-yl)acetic acidHCID 22712059HCID 22712059, compound

Product 1

HCID 9880843HCID 9880843, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

230 mg of 2-(3′-fluoro-biphenyl-4-yl)-acetic acid is dissolved in 5 ml of tetrahydrofuran, mixed with 0.11 ml of oxalyl chloride and one drop of dimethylformamide, and stirred for 2 hours at room temperature. 62 mg of 1,4,5,6-tetrahydro-cyclopentapyrazol-3-yl-amine is added to this solution. The mixture is stirred for 12 hours at room temperature and then concentrated by evaporation. The residue is extracted with ethyl acetate. The extract is washed with sodium bicarbonate solution and water, dried on magnesium sulfate and concentrated by evaporation. The brown residue is dissolved in 5 ml of methanol and mixed with 0.1 ml of a 30% sodium methylate solution. It is stirred for 4 hours at room temperature and then concentrated by evaporation. The residue is extracted with ethyl acetate. The extract is washed with sodium bicarbonate solution and sodium chloride solution, dried on magnesium sulfate and concentrated by evaporation. A yellow, resinous oil is obtained that is purified by HPLC. 2-(3′-Fluoro-biphenyl-4-yl)-N-(1,4,5,6-tetrahydro-cyclopentapyrazol-3-yl)-acetamide with a melting point of 180-181° C. is obtained.

Workup

  1. stirringThe mixture is stirred for 12 hours at room temperature
  2. concentrationconcentrated by evaporation
  3. extractionThe residue is extracted with ethyl acetate
  4. washThe extract is washed with sodium bicarbonate solution and water
  5. customdried on magnesium sulfate
  6. concentrationconcentrated by evaporation
  7. dissolutionThe brown residue is dissolved in 5 ml of methanol
  8. additionmixed with 0.1 ml of a 30% sodium methylate solution
  9. stirringIt is stirred for 4 hours at room temperature
  10. concentrationconcentrated by evaporation
  11. extractionThe residue is extracted with ethyl acetate
  12. washThe extract is washed with sodium bicarbonate solution and sodium chloride solution
  13. customdried on magnesium sulfate
  14. concentrationconcentrated by evaporation
  15. customA yellow, resinous oil is obtained
  16. customthat is purified by HPLC

Sources & evidence

ORD record
ord-87d85bfe71ed464f99d0d5f8ee2c90b3
Source dataset
uspto-grants-2004_06
Patent number
US06747046B2

Reaction notes

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