tert-butyl 5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydropyridine-1(2H)-carboxylate → Tert-butyl 3-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)piperidine-1-carboxylate

HRID 1972734Notes

Reaction equation

HRID 1972734 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]3[CH2:12][CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[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[CH2:12][CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 58529940tert-butyl 5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 58529279Tert-butyl 3-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)piperidine-1-carboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To a dry flask purged with N2 was added platinum (IV) oxide (150 mg, 0.66 mmol) followed by tert-butyl 5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydropyridine-1(2H)-carboxylate (2.09 mg, 6.63 mmol) as a solution in acetic acid (60 mL). The mixture was stirred under an H2 atmosphere for 64 h. The mixture was filtered through a pad of Celite® rinsing with acetic acid and EtOH. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (200 mL). The organic mixture was washed with saturated, aqueous NaHCO3 (200 mL) followed by brine, and was dried (Na2SO4) and concentrated to dryness to afford 1.60 g (76%) of the desired product. ES-MS m/z 318.22 [M+H]+, HPLC RT (min) 2.43.

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 EtOH
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  6. washThe organic mixture was washed with saturated, aqueous NaHCO3 (200 mL)
  7. dry with materialwas dried (Na2SO4)
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-37c014f8d8764e568973dc1773842f08
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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