Calcium Sulfate → HCID 21906405, compound

HRID 1883049Notes

Reaction equation

HRID 1883049 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:29])[C:10]2[CH:15]=[C:14](I)[CH:13]=[CH:12][C:11]=2[NH:17][C:18]([CH:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:22][CH2:21]2)=[O:19])=[N:6][CH:7]=1.[CH:30]([O-])=[O:31].[Na+].S([O-])([O-])(=O)=O.[Ca+2]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:29])[C:10]2[CH:15]=[C:14]([CH:30]=[O:31])[CH:13]=[CH:12][C:11]=2[NH:17][C:18]([CH:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:22][CH2:21]2)=[O:19])=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 24497Calcium SulfateHCID 2723810Sodium FormateHCID 21906277N-(5-chloropyridin-2-yl)-5-iodo-2-[(1-isopropylpiperidin-4-ylcarbonyl)amino]benzamide

Product 1

HCID 21906405HCID 21906405, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of N-(5-chloropyridin-2-yl)-5-iodo-2-[(1-isopropylpiperidin-4-ylcarbonyl)amino]benzamide (0.51 g, 0.97 mmol) in N,N-dimethylformamide (10 mL) was added sodium formate (0.11 g, 1.6 mmol), calcium sulfate (0.39 g, 2.9 mmol), triphenylphosphine (6 mg, 0.02 mmol) and dichlorobis(triphenylphosphine)palladium(II) (15 mg, 0.02 mmol). The reaction mixture was heated to 80° C., stirred overnight, cooled to room temperature, partitioned between dichloromethane and saturated aqueous sodium bicarbonate, and the layers separated. The organic phase was filtered to remove solids, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by RPHPLC, eluting with a gradient of 10% through 50% acetonitrile in 0.05% aqueous hydrochloric acid, to give 0.14 g (31%) of a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between dichloromethane and saturated aqueous sodium bicarbonate
  3. customthe layers separated
  4. filtrationThe organic phase was filtered
  5. customto remove solids
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by RPHPLC
  10. washeluting with a gradient of 10% through 50% acetonitrile in 0.05% aqueous hydrochloric acid

Sources & evidence

ORD record
ord-1cbc957fe6d141788f1f5ef6d3f6f1b7
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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