Pyridine → HCID 68545460, compound

HRID 2245828Notes

Reaction equation

HRID 2245828 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:33]=1[NH:32][CH2:31][N:30]([CH:34]([CH3:36])[CH3:35])[C:29]2=[O:37].N1C=CC=CC=1.C1CN2C(=NCCC2)NC1>ClCCl.CN(C)C=O>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([N:32]2[C:33]3[C:28](=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:23])[C:29](=[O:37])[N:30]([CH:34]([CH3:36])[CH3:35])[CH2:31]2)=[O:9])[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1

Participants

8

Reactant 5

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 79873TriazabicyclodeceneHCID 115875353-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid2×HCID 68546671HCID 68546671, compound

Product 1

HCID 68545460HCID 68545460, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (787 mg, 2.45 mmol) (i.e. the product of Example 1, Step D) in dichloromethane (10 mL) was added dimethylformamide (20 μL) and oxalyl chloride (235 μL). The mixture was stirred for 1 hour, at which point it had become clear. After removing volatiles under reduced pressure, the residue was dissolved in dichloromethane (5 mL) and one half of the solution was added to a mixture of the product of Step A (0.25 g, 1.2 mmol) and pyridine (148 μL, 1.8 mmol) in methylene chloride (10 mL). After stirring at ambient temperature overnight, 1,5,7-triazabicyclo[4.4.0]dec-5-ene bound to polystyrene crosslinked with 2% DVB (1 g) (Fluka Chemie AG catalog number 90603) was added and the mixture was stirred for an additional 15 minutes. The mixture was then filtered and concentrated under reduced pressure. The resulting residue was purified by chromatography on silica gel to give the title compound, a compound of the invention, as a white solid (0.18 g).

Workup

  1. customAfter removing volatiles under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane (5 mL)
  3. stirringAfter stirring at ambient temperature overnight
  4. additionwas added
  5. stirringthe mixture was stirred for an additional 15 minutes
  6. filtrationThe mixture was then filtered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d2e6dd5c9cea4e1b9cb3aeddab5aa851
Source dataset
uspto-grants-2010_03
Patent number
US07683201B2

Reaction notes

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