HCID 66600285, compound → HCID 59548465, compound

HRID 1621615Notes

Reaction equation

HRID 1621615 reaction equation
[F:1][CH:2]([F:43])[O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[C:16]([C:17]3[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([N:24](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)[N:18]=3)=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1>C(O)(C(F)(F)F)=O.CS(C)=O>[F:43][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[C:16]([C:17]3[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH2:24])[N:18]=3)=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 66600285HCID 66600285, compound

Product 1

HCID 59548465HCID 59548465, compoundYield 3.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(2-(3-(difluoromethoxy)phenylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.121 g, 0.207 mmol) in TFA (8.0 mL) (Aldrich) was heated at 80° C. overnight using a hotplate and a metal heating block. The crude product was dissolved in 2.5 mL of DMSO, and was purified by reversed phase chromatography (Gilson; 10-90% CH3CN in water with TFA additive: 0.1% v/v in each solvent). The fractions were combined and the CH3CN was removed. DCM was added and the whole was washed with a saturated solution of NaHCO3 (1×), brine (1×), dried over MgSO4, filtered and concentrated to give 4-(2-(3-(difluoromethoxy)phenylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (24 mg, 6.97 μmol, 3.37% yield) as a yellow amorphous solid. 1H NMR (400 MHz, CDCl3) δ 12.17 (br. s., 1H); 8.80 (d, J=8.2 Hz, 1H); 8.41 (br. s., 1H); 7.97 (br. s., 1H); 7.83-7.90 (m, 1H); 7.78 (br. s., 1H); 7.62 (d, J=8.6 Hz, 1H); 7.31-7.40 (m, 1H); 6.93-7.01 (m, 1H); 6.78 (d, J=8.2 Hz, 1H); 2.45 (br. s., 3H). m/z (ESI, +ve ion) 345.1 (M+H)+.

Workup

  1. temperaturea metal heating block
  2. customwas purified by reversed phase chromatography (Gilson
  3. customthe CH3CN was removed
  4. additionDCM was added
  5. washthe whole was washed with a saturated solution of NaHCO3 (1×), brine (1×)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-51a58b6bd86f4cf78fac537b669aed4f
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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