HCID 59231991, compound → HCID 59232077, compound

HRID 1099269Notes

Reaction equation

HRID 1099269 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]3[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH:16]=3)[N:6]2[N:5]=[CH:4][N:3]=1>C(O)(=O)C.[Pt](=O)=O>[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 59231991HCID 59231991, compound

Product 1

HCID 59232077HCID 59232077, compoundYield 103.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To a dry flask purged with N2 was added platinum(IV) oxide (127 mg, 0.56 mmol) followed by tert-butyl 4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,6-dihydropyridine-1(2H)-carboxylate (587 mg, 1.86 mmol) as a solution in acetic acid (19 mL). The mixture was stirred under an H2 atmosphere for 16 h. The mixture was filtered through a pad of Celite® rinsing with acetic acid and ethanol. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (100 mL). The organic was washed with saturated aqueous NaHCO3 (2×75 mL) and the aqueous mixture was back extracted with ethyl acetate (3×50 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated to dryness to afford 610 mg (100%) of the desired product as a gray solid.

Workup

  1. customTo a dry flask purged with N2
  2. filtrationThe mixture was filtered through a pad of Celite®
  3. washrinsing with acetic acid and ethanol
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  6. washThe organic was washed with saturated aqueous NaHCO3 (2×75 mL)
  7. extractionthe aqueous mixture was back extracted with ethyl acetate (3×50 mL)
  8. washThe combined organics were washed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-63deb1271bc84f1cbd8d68c1c236e0f5
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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