Oxalyl chloride → HCID 59516100, compound

HRID 1799386Notes

Reaction equation

HRID 1799386 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([S:16][CH2:17][CH2:18][CH3:19])=[C:14]([C:20]([OH:22])=O)[CH:13]=[N:12]2)=[CH:7][CH:6]=1)=[O:4].C(Cl)(=O)C(Cl)=O.Cl.[F:30][C:31]([F:44])([F:43])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH:38]1[CH2:42][CH2:41][NH:40][CH2:39]1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C.O>[CH2:17]([S:16][C:15]1[N:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=2)[N:12]=[CH:13][C:14]=1[C:20]([N:40]1[CH2:41][CH2:42][CH:38]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[C:31]([F:30])([F:43])[F:44])[CH2:39]1)=[O:22])[CH2:18][CH3:19]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 450739823-(2-(Trifluoromethyl)phenyl)pyrrolidine hydrochlorideHCID 595161221-(4-Methoxycarbonylphenyl)-5-propylsulfanyl-pyrazole-4-carboxylic acid2×

Product 1

HCID 59516100HCID 59516100, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1-(4-methoxycarbonylphenyl)-5-propylsulfanyl-pyrazole-4-carboxylic acid (Intermediate #7) was dissolved in DCM (3 mL). 1 drop of DMF and oxalyl chloride to (71 μL, 0.83 mmol) was added. The mixture was stirred at ambient temperature for 2 h and then volatiles were removed by evaporation under reduced pressure. The residue was dissolved in DCM (5 mL) and added to a solution of 3-[2-(trifluoromethyl)phenyl]pyrrolidine HCl (105 mg, 0.42 mmol) and DIPEA (217 μL, 1.25 mmol) in DCM (5 mL). Water (10 mL) was added and the mixture stirred vigorously and passed through a phase separating column. The filtrate was purified by chromatography on silica gel, eluting with 0-20% EtOAc/DCM to give the title compound as a clear colourless oil (177 mg, 81%).

Workup

  1. customvolatiles were removed by evaporation under reduced pressure
  2. dissolutionThe residue was dissolved in DCM (5 mL)
  3. stirringthe mixture stirred vigorously
  4. customseparating column
  5. customThe filtrate was purified by chromatography on silica gel
  6. washeluting with 0-20% EtOAc/DCM

Sources & evidence

ORD record
ord-821f1333ff9b4027949d7be249b5d804
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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