HCID 58529715, compound → HCID 58529895, compound

HRID 1972738Notes

Reaction equation

HRID 1972738 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:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=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:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 58529715HCID 58529715, compound

Product 1

HCID 58529895HCID 58529895, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 176Acetic AcidSolvent

Procedure

To a dry flask purged with N2 was added platinum (IV) oxide (114 mg, 0.50 mmol) followed by tert-butyl 5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate (1.66 mg, 5.04 mmol) as a solution in acetic acid (25 mL). The mixture was stirred under an H2 atmosphere for 16 h. Additional platinum (IV) oxide (114 mg, 0.50 mmol) was added and the reaction continued to stir under an H2 atmosphere for 20 h. The mixture was filtered through a pad of Celite® rinsing with acetic acid. The filtrate was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (200 mL). The organic mixture was washed with saturated, aqueous NaHCO3 (1×200 mL) and the aqueous mixture was back extracted with ethyl acetate (2×75 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to dryness to afford 1.44 g (86%) of the desired product. ES-MS m/z 332.11 [M+H]+, HPLC RT (min) 2:46.

Workup

  1. customTo a dry flask purged with N2
  2. stirringto stir under an H2 atmosphere for 20 h
  3. filtrationThe mixture was filtered through a pad of Celite®
  4. washrinsing with acetic acid
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  7. washThe organic mixture was washed with saturated, aqueous NaHCO3 (1×200 mL)
  8. extractionthe aqueous mixture was back extracted with ethyl acetate (2×75 mL)
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fde99c1425ae4e11b431c4cc98bbcca0
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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