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Home > Encyclopedia > Methanesulfonamide, N-[3-[[[2-[(2,3-dihydro-2-oxo-1H-indol-5-yl)amino]-5-(trifluoromethyl)-4-pyrimidinyl]amino]methyl]-2-pyridinyl]-N-methyl-, benzenesulfonate (1:1)

Methanesulfonamide, N-[3-[[[2-[(2,3-dihydro-2-oxo-1H-indol-5-yl)amino]-5-(trifluoromethyl)-4-pyrimidinyl]amino]methyl]-2-pyridinyl]-N-methyl-, benzenesulfonate (1:1)

Methanesulfonamide, N-[3-[[[2-[(2,3-dihydro-2-oxo-1H-indol-5-yl)amino]-5-(trifluoromethyl)-4-pyrimidinyl]amino]methyl]-2-pyridinyl]-N-methyl-, benzenesulfonate (1:1) structure

Methanesulfonamide, N-[3-[[[2-[(2,3-dihydro-2-oxo-1H-indol-5-yl)amino]-5-(trifluoromethyl)-4-pyrimidinyl]amino]methyl]-2-pyridinyl]-N-methyl-, benzenesulfonate (1:1) 

structure
  • CAS No:

    939791-38-5

  • Formula:

    C21H20F3N7O3S.C6H6O3S

  • Chemical Name:

    Methanesulfonamide, N-[3-[[[2-[(2,3-dihydro-2-oxo-1H-indol-5-yl)amino]-5-(trifluoromethyl)-4-pyrimidinyl]amino]methyl]-2-pyridinyl]-N-methyl-, benzenesulfonate (1:1)

  • Synonyms:

    Methanesulfonamide,N-[3-[[[2-[(2,3-dihydro-2-oxo-1H-indol-5-yl)amino]-5-(trifluoromethyl)-4-pyrimidinyl]amino]methyl]-2-pyridinyl]-N-methyl-,benzenesulfonate (1:1);PF 00562271

  • Categories:

    Biochemical Engineering  >  Inhibitors

Methanesulfonamide, N-[3-[[[2-[(2,3-dihydro-2-oxo-1H-indol-5-yl)amino]-5-(trifluoromethyl)-4-pyrimidinyl]amino]methyl]-2-pyridinyl]-N-methyl-, benzenesulfonate (1:1) Basic Attributes

665.6638496

665.134

-0

Characteristics

200

6.51540

Methanesulfonamide, N-[3-[[[2-[(2,3-dihydro-2-oxo-1H-indol-5-yl)amino]-5-(trifluoromethyl)-4-pyrimidinyl]amino]methyl]-2-pyridinyl]-N-methyl-, benzenesulfonate (1:1) Use and Manufacturing

Methods of Manufacturing

To a Naljug, benzenesulfonic acid (1.8 kg, 1.5 eq.) and water (2 L) were added and agitated until the solution was homogeneous. The solution was then added to the reactor under speck free conditions. The product of step 3, the free base of Formula I (3.8 kg) was charged to a separate reactor followed by ethanol/water (20 gal/15 gal), the heated to 70° C. The hot slurry was transferred to the reactor containing the salt solution under speck free conditions. The reactor was cooled to 20-30° C. over 2 hrs then held between 20-30° C. for 12 hours. No solids were collected upon the first filtration. The solution was returned to the reactor under speck free conditions and the reactor cooled to 10-20° C. Material rapidly crystallized out of solution and was granulated for 12 hours. The slurry was filtered through a Nutche filter and the solids were isolated and dried for 24 hours at 20-30° C. The material was milled using the Bantam Mill. The final amount isolated was 4.02 kg, overall yield 82percent.

Uses

A potent, ATP-competitive and reversible inhibitor of FAK and Pyk2 catalytic activity with IC50s of 1.5 nM and 14 nM, respectively.

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