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Trifluoromethanesulfonic acid → 4-(5-Chloro-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

HRID 1812392
Notes
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Reaction equation

HRID 1812392 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:18]2[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([N:25](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[N:19]=2)[C:5]([NH:8][C:9]2[CH:10]=[N:11][C:12]([O:16][CH3:17])=[C:13]([F:15])[CH:14]=2)=[N:6][CH:7]=1.FC(F)(F)S(O)(=O)=O>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:18]2[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH2:25])[N:19]=2)[C:5]([NH:8][C:9]2[CH:10]=[N:11][C:12]([O:16][CH3:17])=[C:13]([F:15])[CH:14]=2)=[N:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 666111934-(5-chloro-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 685176504-(5-Chloro-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

4-(5-chloro-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (1.35 g, 2.242 mmol) (Example 313, Step 2) was dissolved in TFA (22 mL), trifluoromethanesulfonic acid (0.587 mL, 6.73 mmol) was added, and the resulting mixture was stirred at 80° C. for 2 h. The reaction mixture was then concentrated, and the residue was taken up in 400 mL of EtOAc, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 4 times with 150 mL of sodium bicarbonate (saturated, aqueous), separated, and concentrated via rotovap to give the title compound as an insoluble yellow solid which was used without further purification. m/z (ESI, +ve ion) 362.0 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additionadded to a separatory funnel
  3. custompartitioned with sodium bicarbonate (saturated, aqueous)
  4. washwashed 4 times with 150 mL of sodium bicarbonate (saturated, aqueous)
  5. customseparated
  6. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-17f4e03d5b2642b5a3a23349470f9076
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362241B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes