Methanesulfonamide → HCID 56592716, compound

HRID 2359272Notes

Reaction equation

HRID 2359272 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:45][S:46]([NH2:49])(=[O:48])=[O:47].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:45][S:46]([NH:49][C:14](=[O:15])[C:13]1[CH:17]=[CH:18][C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:20])([F:19])[F:1])[CH:4]=2)=[CH:11][CH:12]=1)(=[O:48])=[O:47]

Participants

6

Reactant 4

HCID 72879Methanesulfonamide2×HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 13105473HCID 13105473, compound

Product 1

HCID 56592716HCID 56592716, compoundYield 170.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(3-(trifluoromethyl)phenylamino)benzoic acid (150 mg, 0.533 mmol) in DMF (4 mL) were added HATU (243 mg, 0.640 mmol), methanesulfonamide (152 mg, 1.60 mmol) and DIPEA (0.296 mL) and the reaction stirred at room temperature for 16 hours. Methanesulfonamide (152 mg, 1.60 mmol) was added and the reaction stirred at room temperature for 72 hours. After this time the reaction was quenched by the addition of potassium hydrogen sulfate (20 mL) and the aqueous extracted with dichlormethane (3×20 mL). The combined organics were washed with brine (40 mL), filtered through a phase separation cartridge and then the solvent was removed under reduced pressure to give an oil (325 mg). The crude was purified by preparative HPLC to give the title compound.

Workup

  1. stirringthe reaction stirred at room temperature for 72 hours
  2. customAfter this time the reaction was quenched by the addition of potassium hydrogen sulfate (20 mL)
  3. extractionthe aqueous extracted with dichlormethane (3×20 mL)
  4. washThe combined organics were washed with brine (40 mL)
  5. filtrationfiltered through a phase separation cartridge
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a856cadb52654557a39311d68f35bc06
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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