HCID 66611387, compound → 4-[6'-[(6-Methoxy-3-pyridinyl)amino][2,3'-bipyridin]-5'-yl]-6-methyl-1,3,5-triazin-2-amine

HRID 1621631Notes

Reaction equation

HRID 1621631 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[CH:17]=[C:18]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)[CH:19]=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[N:10]=2)=CC=1>C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]2[CH:17]=[C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[CH:19]=[N:20][C:21]=2[NH:22][C:23]2[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[N:10]=1

Participants

3

Reactant 1

HCID 66611387HCID 66611387, compound

Product 1

HCID 595481784-[6'-[(6-Methoxy-3-pyridinyl)amino][2,3'-bipyridin]-5'-yl]-6-methyl-1,3,5-triazin-2-amineYield 41%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5′-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxypyridin-3-yl)-2,3′-bipyridin-6′-amine (0.0419 g, 0.067 mmol) in TFA (3.0 mL) (Aldrich) was heated at 80° C. overnight. The solution was cooled to room temperature and concentrated. The crude residue was treated with 2M NH3 in MeOH and dry-packed with silica gel. Purification on an ISCO Combiflash Companion (12 g column, 1-15% MeOH in DCM over 25 min, product eluted with 10% MeOH)) gave 5′-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxypyridin-3-yl)-2,3′-bipyridin-6′-amine (0.0106 g, 0.027 mmol, 41.0% yield) as a yellow amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 11.98 (s, 1H); 9.53 (d, J=2.5 Hz, 1H); 9.00 (d, J=2.5 Hz, 1H); 8.67 (d, J=5.3 Hz, 1H); 8.58 (d, J=2.7 Hz, 1H); 8.21 (dd, J=9.0, 2.9 Hz, 1H); 7.96 (t, J=7.8 Hz, 2H); 7.88 (td, J=7.6, 1.8 Hz, 1H); 7.76 (d, J=2.7 Hz, 1H); 7.33 (s, 1H); 6.86 (d, J=9.0 Hz, 1H); 3.86 (s, 3H); 2.47 (s, 3H). m/z (ESI, +ve ion) 387.0 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additionThe crude residue was treated with 2M NH3 in MeOH and dry-packed with silica gel
  3. customPurification
  4. washon an ISCO Combiflash Companion (12 g column, 1-15% MeOH in DCM over 25 min, product eluted with 10% MeOH))

Sources & evidence

ORD record
ord-0790ebcc2684470fa7eec39728421937
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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