Dimethyl ((R)-4-Oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)aspartate

Ref. TR-D414760

Product Information

• Name: Dimethyl ((R)-4-Oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)aspartate
• Synonyms: dimethyl 2-[[(2R)-4-oxo-4-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-1-(2,4,5-trifluorophenyl)butan-2-yl]amino]butanedioate

Description

Applications Dimethyl ((R)-4-Oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)aspartate is an intermediate in the synthesis of (R)-Sitagliptin rac-Fumarate Adduct (S491040) which is an impurity of Sitagliptin (S491000), a trizolopyrazine dipeptidyl peptidase IV inhibitor. Sitagliptin has recently been approved for the therapy of type II diabetes.
References Kim, D., et al.: J. Med. Chem. 48, 141 (2005), Ahren, B., et al.: Eur. J. Pharmacol. 521 164 (2005), Bergman, A., et al: Clin. Ther. 28, 55 (2006)

• Brand: TRC

Chemical properties

• Molecular weight: 551.439
• Formula: C₂₂H₂₃F₆N₅O₅
• Color/Form: Neat
• InChI: InChI=1S/C22H23F6N5O5/c1-37-19(35)9-16(20(36)38-2)29-12(5-11-6-14(24)15(25)8-13(11)23)7-18(34)32-3-4-33-17(10-32)30-31-21(33)22(26,27)28/h6,8,12,16,29H,3-5,7,9-10H2,1-2H3/t12-,16?/m1/s1
• InChI key: InChIKey=RVAGHSBDBUQPJZ-ZGTOLYCTSA-N
• SMILES: COC(=O)CC(N[C@@H](CC(=O)N1CCn2c(nnc2C(F)(F)F)C1)Cc1cc(F)c(F)cc1F)C(=O)OC