Trifluoroacetic acid → HCID 59548364, compound

HRID 1621783Notes

Reaction equation

HRID 1621783 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([C:15]3[C:16]([NH:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([O:28]CC5C=CC(OC)=CC=5)[CH:23]=4)=[N:17][CH:18]=[CH:19][CH:20]=3)[N:12]=[C:11]([CH3:38])[N:10]=2)=CC=1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.C([O-])(O)=O.[Na+]>>[NH2:8][C:9]1[N:10]=[C:11]([CH3:38])[N:12]=[C:13]([C:15]2[C:16]([NH:21][C:22]3[CH:27]=[CH:26][NH:25][C:24](=[O:28])[CH:23]=3)=[N:17][CH:18]=[CH:19][CH:20]=2)[N:14]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 66611533HCID 66611533, compound

Product 1

HCID 59548364HCID 59548364, compoundYield 18.5%

Procedure

A solution of N,N-bis(4-methoxybenzyl)-4-(2-(2-(4-methoxybenzyloxy)pyridin-4-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.120 g, 0.183 mmol) in trifluoroacetic acid (Aldrich) (1.631 mL, 21.96 mmol) and trifluoromethane sulfonic acid (TCI) (0.810 mL, 9.15 mmol) was heated at 80° C. in a sealed tube for 1 h. The reaction mixture was neutralized with sat. NaHCO3.The precipitate was collected by filtration. The precipitate was purified by prep HPLC to give the product as a white solid (0.010 g). m/z (ESI, +ve ion) 296.1 (M+H)+. 1H NMR (300 MHz, d6-DMSO) δ 12.14 (s, 1H); 10.94 (br. s., 1H); 8.81 (d, J=6.87Hz, 1H); 8.46 (d, J=4.09 Hz, 1H); 7.66-8.04 (m, 2H); 7.24 (d, J=7.31 Hz, 1H); 7.19 (s, 1H); 7.08 (dd, J=7.97, 4.75 Hz, 1H); 6.53 (d, J=5.70 Hz, 1H); 2.44 (s, 3H).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customThe precipitate was purified by prep HPLC

Sources & evidence

ORD record
ord-40d5956f7e584c67a7a5741165fbf0af
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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