HCID 66610744, compound → HCID 59548204, compound

HRID 1621617Notes

Reaction equation

HRID 1621617 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]=[CH:25][C:26]5[O:30][C:29]([CH3:31])=[N:28][C:27]=5[CH:32]=4)=[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]=[CH:25][C:26]4[O:30][C:29]([CH3:31])=[N:28][C:27]=4[CH:32]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)[N:10]=1

Participants

3

Reactant 1

HCID 66610744HCID 66610744, compound

Product 1

HCID 59548204HCID 59548204, compoundYield 1.6%

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-methylbenzo[d]oxazol-5-amine (0.116 g, 0.202 mmol) in TFA (8.0 mL) (Aldrich) was heated at 80° C. overnight. The TFA was removed in vacuo. The crude product was dissolved in 4 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. The compound and impurities had co-eluted. The material was purified by flash column chromatography using an ISCO Combiflash Companion (4 g column; 1-10% MeOH in DCM over 40 minutes). The compound and impurities co-eluted. The crude product was dissolved in 4 mL of DMSO. Purification by reversed phase chromatography (Gilson; 10-90% CH3CN in water with NH4OH additive: 0.1% v/v in each solvent) followed by drying in a Genevac Series II System gave N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl)-2-methylbenzo[d]oxazol-5-amine (1.079 mg, 3.24 μmol, 1.6% yield) as a yellow amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 12.04 (s, 1H); 8.79 (dd, J=7.7, 2.1 Hz, 1H); 8.37 (dd, J=4.7, 2.0 Hz, 1H); 8.33 (d, J=2.0 Hz, 1H); 7.86 (q, J=3.2 Hz, 1H); 7.70-7.77 (m, 1H); 7.62-7.68 (m, 1H); 7.54-7.60 (m, 1H); 6.91 (dd, J=7.8, 4.7 Hz, 1H); 2.60 (s, 3H); 2.45 (s, 4H). m/z (ESI, +ve ion) 334.1 (M+H)+.

Workup

  1. customThe TFA was removed in vacuo
  2. dissolutionThe crude product was dissolved in 4 mL of DMSO
  3. customwas purified by reversed phase chromatography (Gilson
  4. customthe CH3CN was removed
  5. additionDCM was added
  6. washthe whole was washed with a saturated solution of NaHCO3 (1×), brine (1×)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe material was purified by flash column chromatography
  11. customan ISCO Combiflash Companion (4 g column; 1-10% MeOH in DCM over 40 minutes)
  12. dissolutionThe crude product was dissolved in 4 mL of DMSO
  13. customPurification by reversed phase chromatography (Gilson
  14. dry with materialby drying in a Genevac Series II System

Sources & evidence

ORD record
ord-ab9a6871be3c4cc5b678c79d9dcca7df
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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