HCID 66611496, compound → HCID 59548375, compound

HRID 1621629Notes

Reaction equation

HRID 1621629 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:22][C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][CH:32]=4)[N:29]=[C:28]([CH3:33])[CH:27]=[CH:26]5)=[N:18][CH:19]=[CH:20][CH:21]=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[C:17]([NH:22][C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[N:29]=[C:28]([CH3:33])[CH:27]=[CH:26]4)=[N:18][CH:19]=[CH:20][CH:21]=2)[N:10]=1

Participants

3

Reactant 1

HCID 66611496HCID 66611496, compound

Product 1

HCID 59548375HCID 59548375, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl)-2-methylquinolin-6-amine (0.116 g, 0.199 mmol) in TFA (5.0 mL) (Aldrich) was heated at 80° C. overnight. The solution was cooled to room temperature, and the mixture was concentrated to about 50% of the original volume. The remaining mixture was pipetted carefully into a saturated solution of NaHCO3, which had been cooled in an ice bath. The resulting precipitate was collected by filtration and washed with water. The solid was then suspended in IPA and the precipitate collected by filtration to give N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl)-2-methylquinolin-6-amine (0.0581 g, 0.169 mmol, 85% yield) as a yellow amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 12.30 (s, 1H); 8.83 (d, J=7.0 Hz, 1H); 8.62 (s, 1H); 8.45 (d, J=2.7 Hz, 1H); 8.15 (d, J=8.4 Hz, 1H); 8.03 (d, J=8.0 Hz, 1H); 7.82-7.93 (m, 2H); 7.80 (br. s., 1H); 7.36 (d, J=8.6 Hz, 1H); 6.99 (dd, J=7.3, 4.8 Hz, 1H); 2.63 (s, 3H); 2.48 (br. s., 3H). m/z (ESI, +ve ion) 344.0 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated to about 50% of the original volume
  2. temperaturehad been cooled in an ice bath
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-2574e8b6c86a4163a683ef9a42b6c4fc
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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