Trifluoroacetic acid → 5-(piperidin-4-yl)-7-(2-(1(S)-phenylethyl)amino-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

HRID 897408Notes

Reaction equation

HRID 897408 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:19]3[CH:20]=[N:21][N:22]=[C:18]3[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)=[C:16]([C:33]3[CH:38]=[CH:37][N:36]=[C:35]([NH:39][C@H:40]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH3:41])[CH:34]=3)[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:8]1[CH2:9][CH2:10][CH:11]([C:14]2[N:19]3[CH:20]=[N:21][N:22]=[C:18]3[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:31])([F:30])[F:32])[CH:24]=3)=[C:16]([C:33]3[CH:38]=[CH:37][N:36]=[C:35]([NH:39][C@H:40]([C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH3:41])[CH:34]=3)[N:15]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 208169055-(1-(t-butoxycarbonyl)piperidin-4-yl)-7-(2-(1(S)-phenylethyl)amino-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

Product 1

HCID 208169165-(piperidin-4-yl)-7-(2-(1(S)-phenylethyl)amino-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(1-(t-butoxycarbonyl)piperidin-4-yl)-7-(2-(1(S)-phenylethyl)amino-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine (0.03 g, 0.05 mmol) and trifluoroacetic acid (1 ml) were combined in methylene chloride (5 ml) and maintained at room temperature for 24 hours. The solution was concentrated and the residue was partitioned between methylene chloride and 10% sodium carbonate. The organic layer was separated, dried over sodium sulfate, filtered and the solvent evaporated to give the product as a syrup; MS m/z (M+H)+ 544.1; C30H28F3N7 require 543.2.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was partitioned between methylene chloride and 10% sodium carbonate
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-d931276ced2144f2b91df3329a6ac91f
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

Loading…