Trifluoroacetic acid → N5-(3-(4-Amino-6-methyl-1,3,5-triazin-2-YL)pyridin-2-YL)-2-chloropyridine-3,5-diamine

HRID 1812196Notes

Reaction equation

HRID 1812196 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[C:17]([NH:22][C:23]4[CH:24]=[C:25]([NH:30]S(C5C=CC(F)=CC=5)(=O)=O)[C:26]([Cl:29])=[N:27][CH:28]=4)=[N:18][CH:19]=[CH:20][CH:21]=3)[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:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]2[C:17]([NH:22][C:23]3[CH:24]=[C:25]([NH2:30])[C:26]([Cl:29])=[N:27][CH:28]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)[N:10]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 86647062N-(5-(3-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-YL)pyridin-2-ylamino)-2-chloropyridin-3-YL)-4-fluorobenzenesulfonamide

Product 1

HCID 59548308N5-(3-(4-Amino-6-methyl-1,3,5-triazin-2-YL)pyridin-2-YL)-2-chloropyridine-3,5-diamineYield 63.4%

Procedure

A solution of N-(5-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide (0.087 g, 0.120 mmol) in trifluoroacetic acid (Aldrich) (0.622 mL, 8.37 mmol) and trifluoromethane sulfonic acid (TCI) (0.265 mL, 2.99 mmol).was heated at 80° C. in a sealed tube for 20 min. The reaction mixture was first neutralized with sat. NaHCO3 and then extracted with CHCl3 (3×15 mL). The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated. The crude product was purified by column chromatography (40 g, 20% to 30% acetone in hexanes) to give the product as a white solid (0.025 g). m/z (ESI, +ve ion) 329.0 (M+H)+. 1H NMR (300 MHz, d6-DMSO) δ 12.01 (s, 1H); 8.79 (d, J=7.16 Hz, 1H); 8.37 (d, J=4.39 Hz, 1H); 7.96 (s, 2H); 7.61-7.88 (m, 2H); 6.96 (dd, J=7.89, 4.82 Hz, 1H); 5.48 (s, 2H); 2.45 (s, 3H).

Workup

  1. extractionextracted with CHCl3 (3×15 mL)
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (40 g, 20% to 30% acetone in hexanes)

Sources & evidence

ORD record
ord-7536b870ef0e40b4ba6e198530df513a
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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