Methyl iodide → HCID 86646913, compound

HRID 2063262Notes

Reaction equation

HRID 2063262 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[N:10][N:11]3[C:16]=2[CH2:15][CH2:14][CH2:13][NH:12]3)[CH:5]=[CH:4][N:3]=1.IC.[C:26](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[N:10][N:11]3[C:16]=2[CH2:15][CH2:14][CH2:13][N:12]3[CH3:26])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86646914HCID 86646914, compound

Product 1

HCID 86646913HCID 86646913, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2-chloro-4-pyrimidinyl)-2-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-b]pyridazine (i.e. the product of Step A) (50.0 mg, 0.15 mmol), iodomethane (0.019 mL, 0.31 mmol) and potassium carbonate (63 mg, 0.46 mmol) in N,N-dimethylformamide (3 mL) was stirred at room temperature for 2 h, followed by at 50° C. for 1 h and then at 100° C. for 2 h. The reaction mixture was diluted with water and extracted with ethyl acetate (3×10 mL). The combined organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by medium pressure liquid chromatography using 20-80% ethyl acetate in hexanes as eluant to give 37.4 mg of the title product, a compound of the present invention, as a white solid.

Workup

  1. waitfollowed by at 50° C. for 1 h
  2. waitat 100° C. for 2 h
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. dry with materialThe combined organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by medium pressure liquid chromatography

Sources & evidence

ORD record
ord-77a2e5ab307d447589683c6c356fe5e9
Source dataset
uspto-grants-2012_10
Patent number
US08288375B2

Reaction notes

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