3-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-YL)-N-(6-methoxypyridin-3-YL)quinolin-2-amine → 3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxypyridin-3-yl)quinolin-2-amine

HRID 1812150Notes

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

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxypyridin-3-yl)quinolin-2-amine (0.16 g, 0.26 mmol) in TFA (3 mL) was treated with a couple of drops of trifluoromethane sulfonic acid. The reaction mixture was stirred at 90° C. for 18 h, allowed to cool to room temperature, and the solvent was removed in vacuo. Purification by reverse-phase preparative HPLC using a Phenomenex Gemini column, 10 micron, C18, 100 Å, 150×30 mm, 0.1% TFA in CH3CN/H2O, gradient 10% to 90% over 18 min gave 3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxypyridin-3-yl)quinolin-2-amine (31 mg, 0.09 mmol, 33% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 11.99 (br. s., 1H); 9.33 (s, 1H); 8.88 (br. s., 1H); 8.42 (d, J=7.43 Hz, 1H); 7.77-8.09 (m, 3H); 7.67 (br. s., 2H); 7.33 (br. s., 1H); 6.87 (d, J=8.80 Hz, 1H); 3.87 (s, 3H); 2.49 (s, 3H). m/z (ESI, +ve ion) 359.9 (M+H)+.

Workup

temperatureto cool to room temperature
customthe solvent was removed in vacuo
customPurification by reverse-phase preparative HPLC
customover 18 min

Sources & evidence

ORD record: ord-455b6d1923ca4ea9a2250eed11d7b96a
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362241B2

Reaction notes

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