HCID 57447016, compound → HCID 57447061, compound

HRID 2366670Notes

Reaction equation

HRID 2366670 reaction equation
[N:1]1([C:7](=[O:30])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:25]3[C:24]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[N:18]=[C:17]([NH2:26])[C:16]=3[N:15]=[C:14]2[CH2:27][CH2:28][CH3:29])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>[Pt](=O)=O.FC(F)(F)C(O)=O>[N:1]1([C:7](=[O:30])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:25]3[C:24]4[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=4[N:18]=[C:17]([NH2:26])[C:16]=3[N:15]=[C:14]2[CH2:27][CH2:28][CH3:29])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 57447016HCID 57447016, compound

Product 1

HCID 57447061HCID 57447061, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1-(6-morpholin-4-yl-6-oxohexyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (2.0 g, 4.9 mmol), platinum (IV) oxide (1.5 g, 6.6 mmol), and trifluoroacetic acid (50 mL) was placed in a Parr vessel and shaken under hydrogen pressure (50 psi, 3.5×105 Pa) for 24 hours. The trifluoroacetic acid was removed under reduced pressure, and the residue was sonicated with 10% aqueous sodium hydroxide. The resulting solid was mixed with material from another run and recrystallized from water. The crystals were isolated by filtration and dried overnight at 80° C. to provide 0.978 g of 1-(6-morpholin-4-yl-6-oxohexyl)-2-propyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as a white crystalline powder, mp 162-163° C.

Workup

  1. customThe trifluoroacetic acid was removed under reduced pressure
  2. customthe residue was sonicated with 10% aqueous sodium hydroxide
  3. additionThe resulting solid was mixed with material from another run
  4. customrecrystallized from water
  5. customThe crystals were isolated by filtration
  6. customdried overnight at 80° C.

Sources & evidence

ORD record
ord-7b6a9fb4b9e84e93b50eb3e3032da47b
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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