HCID 66611960, compound → HCID 59548452, compound

HRID 1621637Notes

Reaction equation

HRID 1621637 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]=[CH:18][C:19]([C:32]4[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=4)=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:30][CH3:31])=[C:27]([F:29])[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]=[CH:18][C:19]([C:32]3[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=3)=[N:20][C:21]=2[NH:22][C:23]2[CH:24]=[N:25][C:26]([O:30][CH3:31])=[C:27]([F:29])[CH:28]=2)[N:10]=1

Participants

3

Reactant 1

HCID 66611960HCID 66611960, compound

Product 1

HCID 59548452HCID 59548452, compoundYield 64.8%

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-(5-fluoro-6-methoxypyridin-3-yl)-2,4′-bipyridin-6-amine (0.139 g, 0.216 mmol) in TFA (8.0 mL) (Aldrich) was heated at 80° C. overnight. The solution was cooled to room temperature and concentrated to about 50% of the original volume under a stream of argon. The remaining mixture was pipetted carefully into a saturated solution of NaHCO3 which had been cooled in an ice bath. The resulting precipitate was removed by filtration and washed with water. The impure solid was suspended in IPA, and the suspension was subjected to filtration. The solid was washed with DMSO, followed by water to give 5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(5-fluoro-6-methoxypyridin-3-yl)-2,4′-bipyridin-6-amine (0.0565 g, 0.140 mmol, 64.8% yield). 1H NMR (400 MHz, d6-DMSO) δ 12.03 (s, 1H); 8.93 (d, J=8.0 Hz, 1H); 8.75 (d, J=5.9 Hz, 2H); 8.54 (d, J=1.8 Hz, 1H); 8.32-8.38 (m, 1H); 8.00 (d, J=5.7 Hz, 2H); 7.95 (br. s., 1H); 7.81 (br. s., 1H); 7.67 (d, J=8.0 Hz, 1H); 3.97 (s, 3H); 2.46 (s, 3H). m/z (ESI, +ve ion) 405.0 (M+H)+.

Workup

  1. concentrationconcentrated to about 50% of the original volume under a stream of argon
  2. temperaturehad been cooled in an ice bath
  3. customThe resulting precipitate was removed by filtration
  4. washwashed with water
  5. filtrationthe suspension was subjected to filtration
  6. washThe solid was washed with DMSO

Sources & evidence

ORD record
ord-bb209cc43e3c4a20b429dcec0c7ea29f
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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