Trifluoromethanesulfonic acid → HCID 59548270, compound

HRID 1621594Notes

Reaction equation

HRID 1621594 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:29][C:30]4[CH:31]=[N:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=4)=[N:17][CH:18]=[C:19]([C:21]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[O:22])[CH:20]=3)[N:12]=[C:11]([CH3:38])[N:10]=2)=CC=1.OS(C(F)(F)F)(=O)=O>C(O)(C(F)(F)F)=O>[CH3:37][O:36][C:33]1[N:32]=[CH:31][C:30]([NH:29][C:16]2[C:15]([C:13]3[N:12]=[C:11]([CH3:38])[N:10]=[C:9]([NH2:8])[N:14]=3)=[CH:20][C:19]([C:21]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[O:22])=[CH:18][N:17]=2)=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 66600185HCID 66600185, compound

Product 1

HCID 59548270HCID 59548270, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

A solution of N,N-bis(4-methoxybenzyl)-4-(2-((6-methoxy-3-pyridinyl)amino)-5-(4-morpholinylcarbonyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine (0.128 g, 0.193 mmol) in TFA (2.00 mL) at ambient temperature was treated with triflic acid (0.051 mL, 0.579 mmol) and heated for 4 h at 80° C. The reaction mixture was concentrated, but not to dryness. A few ice cubes were added and saturated NaHCO3 (aq.) was added until pH was about 7. The solid was collected by filtration, washed with water and CH2Cl2, and dried under vacuum to give 4-(2-((6-methoxy-3-pyridinyl)amino)-5-(4-morpholinylcarbonyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine (0.056 g, 0.133 mmol, 68.6% yield) as a brown solid. 1H NMR (400 MHz, d6-DMSO) δ 11.92 (s, 1H); 8.87 (s, 1H); 8.52 (s, 1H); 8.38 (s, 1H); 8.11-8.22 (m, 1H); 7.92 (br. s., 1H); 7.78 (br. s., 1H); 6.85 (d, J=8.80 Hz, 1H); 3.84 (s, 3H); 3.54-3.65 (m, 8H); 2.44 (s, 3H). m/z (ESI, +ve ion) 423.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionA few ice cubes were added
  3. additionsaturated NaHCO3 (aq.) was added until pH was about 7
  4. filtrationThe solid was collected by filtration
  5. washwashed with water and CH2Cl2
  6. customdried under vacuum

Sources & evidence

ORD record
ord-f0a603c515e24c2caaf2d2147dce3653
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

Loading…