HCID 59231939, compound → HCID 59232074, compound

HRID 1099267Notes

Reaction equation

HRID 1099267 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]3[CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH:15]=3)[N:6]2[N:5]=[CH:4][N:3]=1>CC(O)=O.[Pt](=O)=O>[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH:11]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 59231939HCID 59231939, compound

Product 1

HCID 59232074HCID 59232074, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of platinum(IV) oxide (2.1 g, 9.5 mmol) and tert-butyl 3-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (11.4 g, 37.8 mmol) in AcOH (150 mL) was stirred for 16 h under a H2 atmosphere. The reaction was purged with N2 and filtered through Celite®, washing with AcOH. After removal of solvent in vacuo, the residue was dissolved in THF:EtOAc and washed with saturated, aqueous sodium carbonate solution. The organic layer was dried and concentrated in vacuo to provide the desired product as a dark solid (10.7 g, 93%). MS: LC/MS (+esi): m/z=304.1 [MH]+; LC/MS rt=2.74 min.

Workup

  1. customThe reaction was purged with N2
  2. filtrationfiltered through Celite®
  3. washwashing with AcOH
  4. customAfter removal of solvent in vacuo
  5. dissolutionthe residue was dissolved in THF
  6. washEtOAc and washed with saturated, aqueous sodium carbonate solution
  7. customThe organic layer was dried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-551c25652e584ada93b46f4c0c040b4a
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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