HCID 66611824, compound → HCID 59548190, compound

HRID 1621703Notes

Reaction equation

HRID 1621703 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([C:15]3[C:16]([NH:28][C:29]4[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=4)=[N:17][CH:18]=[C:19]([CH2:21][N:22]4[CH2:27][CH2:26][S:25][CH2:24][CH2:23]4)[CH:20]=3)[N:12]=[C:11]([CH3:37])[N:10]=2)=CC=1>C(O)(C(F)(F)F)=O.OS(C(F)(F)F)(=O)=O>[CH3:36][O:35][C:32]1[N:31]=[CH:30][C:29]([NH:28][C:16]2[C:15]([C:13]3[N:12]=[C:11]([CH3:37])[N:10]=[C:9]([NH2:8])[N:14]=3)=[CH:20][C:19]([CH2:21][N:22]3[CH2:27][CH2:26][S:25][CH2:24][CH2:23]3)=[CH:18][N:17]=2)=[CH:34][CH:33]=1

Participants

4

Reactant 1

HCID 66611824HCID 66611824, compound

Product 1

HCID 59548190HCID 59548190, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 62406Trifluoromethanesulfonic acidCatalystHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

A solution of N,N-bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)-5-(thiomorpholinomethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (86 mg, 0.129 mmol) in 2 mL of TFA was treated with 2 drops of triflic acid. The brown solution was heated in an oil bath at 80° C. for 5 h. The volatiles were removed on and the dark residue was basified with 1 N NaOH and extracted with EtOAc twice followed by DCM once. The combined organic extracts were concentrated and purified on a Redi-Sep pre-packed silica gel column (12 g) eluting with a gradient of 2-6% MeOH in DCM to give 4-(2-(6-methoxypyridin-3-ylamino)-5-(thiomorpholinomethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (30 mg, 55% yield) as an orange crystalline solid. 1H NMR (400 MHz, d6-DMSO) δ 11.75 (1H, s); 8.68 (1H, d, J=2.4Hz); 8.54 (1H, d, J=2.7 Hz); 8.18 (1H, d, J=2.5 Hz); 8.16 (1H, d J=2.9 Hz); 7.87 (1H, br. s); 7.73 (1H, br. s); 6.82 (1H, d, J=9.0 Hz); 3.84 (3H, s); 3.46 (2H, s); 2.67-2.60 (8H, m); 2.44 (3H, s). m/z (ESI, +ve ion) 425 (M+H)+.

Workup

  1. customThe volatiles were removed on and the dark residue
  2. extractionextracted with EtOAc
  3. concentrationThe combined organic extracts were concentrated
  4. custompurified on a Redi-Sep pre-packed silica gel column (12 g)
  5. washeluting with a gradient of 2-6% MeOH in DCM

Sources & evidence

ORD record
ord-5fb43410178749e0b77163476cbfdb15
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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