HCID 66611464, compound → HCID 59548445, compound

HRID 1812033Notes

Reaction equation

HRID 1812033 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][C:7]=1[O:8][CH3:9]>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

3

Reactant 1

HCID 66611464HCID 66611464, compound

Product 1

HCID 59548445HCID 59548445, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(2-(3-fluoro-4-methoxyphenylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.1253 g, 0.221 mmol) in TFA (8.0 mL) (Aldrich) was heated at 80° C. overnight. The TFA was removed in vacuo and the residue was treated with a saturated solution of NaHCO3. The mixture was extracted with DCM (3×15 mL) and concentrated. The crude brown oil was dissolved in 2.5 mL of DMSO and purified by reversed phase chromatography (Gilson, 10-90% CH3CN in water with NH4OH additive: 0.1% v/v in each solvent). The fractions were concentrated in a Genevac Series II System to give 4-(2-(3-fluoro-4-methoxyphenylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (3.3 mg, 10.11 μmol, 4.57% yield) as a yellow amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 11.91 (s, 1H); 8.77 (dd, J=7.8, 2.0 Hz, 1H); 8.35 (dd, J=4.7, 2.0 Hz, 1H); 7.94 (dd, J=14.2, 2.6 Hz, 1H); 7.48-7.53 (m, 1H); 7.11 (t, J=9.4 Hz, 1H); 6.90 (dd, J=7.8, 4.7 Hz, 1H); 3.82 (s, 3H); 2.43 (s, 3H). m/z (ESI, +ve ion) 327.1 (M+H)+.

Workup

  1. customThe TFA was removed in vacuo
  2. additionthe residue was treated with a saturated solution of NaHCO3
  3. extractionThe mixture was extracted with DCM (3×15 mL)
  4. concentrationconcentrated
  5. dissolutionThe crude brown oil was dissolved in 2.5 mL of DMSO
  6. custompurified by reversed phase chromatography (Gilson, 10-90% CH3CN in water with NH4OH additive
  7. concentrationThe fractions were concentrated in a Genevac Series II System

Sources & evidence

ORD record
ord-fcce7544c3f942a5934b4f4b3d424a07
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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