Tert-butyl (4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate → N-((5-((2-aminopyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)pivalamide

HRID 626542Notes

Reaction equation

HRID 626542 reaction equation
[C:1]([NH:7][C:8](=[O:31])[NH:9][C:10]1[N:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23]C(=O)OC(C)(C)C)[CH:18]=2)=[CH:12][CH:11]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>C(O)(C(F)(F)F)=O>[NH2:23][C:19]1[CH:18]=[C:17]([O:16][C:13]2[CH:12]=[CH:11][C:10]([NH:9][C:8]([NH:7][C:1](=[O:6])[C:2]([CH3:4])([CH3:3])[CH3:5])=[O:31])=[N:15][CH:14]=2)[CH:22]=[CH:21][N:20]=1

Participants

3

Reactant 1

HCID 131735224Tert-butyl (4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate

Product 1

HCID 90409811N-((5-((2-aminopyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)pivalamideYield 100%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl (4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate (1.6 g, 3.73 mmol) was suspended in TFA (20 mL), stirred at RT for 45 min, then concentrated to dryness. The residue was suspended in THF, treated with satd. NaHCO3 and the layers separated. The aqueous layer was diluted with brine, extracted with THF (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford crude N-((5-((2-aminopyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)pivalamide (100% yield assumed) which was used without further purification. MS (ESI) m/z: 330.2 (M+H+).

Workup

  1. concentrationconcentrated to dryness
  2. additiontreated with satd
  3. customNaHCO3 and the layers separated
  4. additionThe aqueous layer was diluted with brine
  5. extractionextracted with THF (3×)
  6. dry with materialthe combined organics were dried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f4b5347c946f4d1c8f6986690d1e51fe
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

Loading…