Trifluoromethanesulfonic acid → HCID 59548270, compound

HRID 1812007Notes

Reaction equation

HRID 1812007 reaction equation
COC1C=CC(C[NH:8][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 71231945(4-Methoxybenzyl)-4-(2-((6-methoxy-3-pyridinyl)amino)-5-(4-morpholinylcarbonyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine

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

Sources & evidence

ORD record
ord-3152795ce6f64cf4a47df038f0d4e9da
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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