yclopropanecarboxylic acid N-[4-[[4-chloro-6-(5-methyl-2H-pyrazol-3-ylamino)pyrimidin-2-yl]sulfanyl]phenyl]amide Chemical Properties

Density 

1.49

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

13.85±0.10(Predicted)

yclopropanecarboxylic acid N-[4-[[4-chloro-6-(5-methyl-2H-pyrazol-3-ylamino)pyrimidin-2-yl]sulfanyl]phenyl]amide Usage And Synthesis

Definition

ChEBI: N-[4-[[4-chloro-6-[(5-methyl-1H-pyrazol-3-yl)amino]-2-pyrimidinyl]thio]phenyl]cyclopropanecarboxamide is an aryl sulfide.

Synthesis

[4-(4,6-Dichloropyrimidin-2-ylsulfonyl)phenyl]methanaminocyclopropanecarboxylic acid (3.0 g, 8.85 mmol) and 3-amino-5-methyl-1H-pyrazole (0.94 g, 9.7 mmol) were mixed in DMF (16 mL) with diisopropylethylamine (1.25 g, 9.7 mmol) and potassium iodide (1.76 g, 10.6 mmol). The reaction mixture was stirred at 50 °C for 6 hours. After completion of the reaction, the solvent was removed by evaporation under reduced pressure and the residue was purified by recrystallization from ethyl acetate. The target product N-[4-[[4-chloro-6-(5-methyl-2H-pyrazol-3-ylamino)pyrimidin-2-yl]sulfonyl]phenyl]aminocyclopropanecarboxylic acid (2.0 g, 91% yield) was obtained as a white solid.LC-MS (m/z): 401 [M + 1]+; 1H NMR (DMSO-d6) δ: 0.82 (d, J = 6.6 Hz, 4H) ), 1.85 (m, 1H), 1.99 (s, 1H), 5.24 (bs, 1H), 6.47 (bs, 1H), 7.55 (m, 2H), 7.71 (m, 2H), 10.22 (s, 1H), 11.95 (s, 1H).

References

[1] Patent: WO2009/86012, 2009, A1. Location in patent: Page/Page column 56; 57
[2] Patent: WO2007/14250, 2007, A2. Location in patent: Page/Page column 18
[3] Patent: WO2008/13807, 2008, A2. Location in patent: Page/Page column 7
[4] Patent: WO2007/136615, 2007, A2. Location in patent: Page/Page column 33-34
[5] Patent: US2009/105270, 2009, A1

yclopropanecarboxylic acid N-[4-[[4-chloro-6-(5-methyl-2H-pyrazol-3-ylamino)pyrimidin-2-yl]sulfanyl]phenyl]amide(639090-55-4)Related Product Information

• yclopropanecarboxylic acid N-[4-[[4-chloro-6-(5-methyl-2H-pyrazol-3-ylamino)pyrimidin-2-yl]sulfanyl]phenyl]amide