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

HRID 1812392Notes

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

Participants

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

concentrationThe reaction mixture was then concentrated
additionadded to a separatory funnel
custompartitioned with sodium bicarbonate (saturated, aqueous)
washwashed 4 times with 150 mL of sodium bicarbonate (saturated, aqueous)
customseparated
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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