HCID 66611911, compound → 4-[6'-Methoxy-6-[(6-methoxy-3-pyridinyl)amino][3,3'-bipyridin]-5-yl]-6-methyl-1,3,5-triazin-2-amine

HRID 1621625Notes

Reaction equation

HRID 1621625 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:32]=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=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:32]=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=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 66611911HCID 66611911, compound

Product 1

HCID 595482294-[6'-Methoxy-6-[(6-methoxy-3-pyridinyl)amino][3,3'-bipyridin]-5-yl]-6-methyl-1,3,5-triazin-2-amineYield 55.2%

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)-6′-methoxy-N-(6-methoxypyridin-3-yl)-3,3′-bipyridin-6-amine (0.163 g, 0.249 mmol) in TFA (8.0 mL) (Aldrich) was heated at 80° C. overnight. The solution was cooled to room temperature, the mixture was concentrated, the crude residue was treated with 2M NH3 in MeOH and dry-packed with silica gel. Purification using an ISCO Combiflash Companion (40 g column; 1-20% MeOH in DCM over 25 min; product eluted with 10% MeOH) afforded 5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6′-methoxy-N-(6-methoxypyridin-3-yl)-3,3′-bipyridin-6-amine (0.0572 g, 0.137 mmol, 55.2% yield) as an orange colored amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 11.81 (s, 1H); 8.98 (d, J=2.7 Hz, 1H); 8.62 (d, J=2.5 Hz, 1H); 8.56 (d, J=2.7 Hz, 1H); 8.47 (d, J=2.3 Hz, 1H); 8.20 (dd, J=8.8, 2.7 Hz, 1H); 8.00 (dd, J=8.6, 2.7 Hz, 1H); 7.90 (br. s., 1H); 7.76 (br. s., 1H); 6.94 (d, J=8.6 Hz, 1H); 6.85 (d, J=8.8 Hz, 1H); 3.90 (s, 3H); 3.86 (s, 3H); 2.46 (s, 3H). m/z (ESI, +ve ion) 417.0 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated
  2. additionthe crude residue was treated with 2M NH3 in MeOH and dry-packed with silica gel
  3. customPurification
  4. washan ISCO Combiflash Companion (40 g column; 1-20% MeOH in DCM over 25 min; product eluted with 10% MeOH)

Sources & evidence

ORD record
ord-ba641ff3a2da49a4b98fe9cb312998c2
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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