Trifluoroacetic acid → 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine

HRID 2366708Notes

Reaction equation

HRID 2366708 reaction equation
[N:1]1([C:7](=[O:29])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[C:24]3[C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[N:17]=[C:16]([NH2:25])[C:15]=3[N:14]=[C:13]2[CH2:26][CH2:27][CH3:28])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>[Pt](=O)=O>[N:1]1([C:7](=[O:29])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[C:24]3[C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[N:17]=[C:16]([NH2:25])[C:15]=3[N:14]=[C:13]2[CH2:26][CH2:27][CH3:28])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 574470661-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 574470931-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amineYield 28%

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

A mixture of 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (1.66 g, 4.19 mmol, prepared in Example 34), platinum (IV) oxide (1.5 g, 6.6 mmol), and trifluoroacetic acid (25 mL) was placed in a Parr vessel and shaken under hydrogen pressure (40 psi, 2.8×105 Pa) overnight. The reaction mixture was filtered through a layer of CELITE filter agent, and the filter cake was washed with ethanol. The filtrate was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol). The resulting solid was triturated three times with 10% aqueous sodium hydroxide, isolated by filtration, and washed with water to provide 0.468 g of 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 158-160° C.

Workup

  1. filtrationThe reaction mixture was filtered through a layer of CELITE filter agent
  2. washthe filter cake was washed with ethanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol)
  5. customThe resulting solid was triturated three times with 10% aqueous sodium hydroxide
  6. customisolated by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-cc223e39e1114ed3850fd03b3aecc87a
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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