HCID 22254499, compound → HCID 12114214, compound

HRID 1839092Notes

Reaction equation

HRID 1839092 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:13]#[C:14][CH2:15][O:16][CH2:17][CH2:18][N:19]1[C:31]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]=[C:23]([NH:32]C(=O)OCC3C=CC=CC=3)[C:22]=2[N:21]=[CH:20]1>[Pt].CO>[CH3:12][NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][N:19]2[C:31]3[C:30]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[N:24]=[C:23]([NH2:32])[C:22]=3[N:21]=[CH:20]2)[CH:4]=1)(=[O:10])=[O:9]

Participants

4

Reactant 1

HCID 22254499HCID 22254499, compound

Product 1

HCID 12114214HCID 12114214, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

Platinum on carbon (0.08 g of 10%) was added to a mixture of benzyl N-(1-{2-[(3-{2-methyl-5-[(methylamino)sulfonyl]phenyl}-2-propynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-yl)carbamate (0.3 g, 0.51 mmol) and methanol (10 mL). The mixture was hydrogenated on a Parr apparatus at 40 psi (2.8 Kg/cm2) for 16 hours. Analysis by LC-MS indicated alkyne reduction but no phenoxycarbonyl removal. Palladium on carbon (0.1 g of 10%) was added and the reaction mixture was hydrogenated at 40 psi (2.8 Kg/cm2) for 8 hours. Analysis by LC-MS indicated only a small amount of phenoxycarbonyl removal. Palladium black (0.1 g) was added and the reaction mixture was hydrogenated at 40 psi (2.8 Kg/cm2) for 16 hours. Analysis by LC-MS indicated one major product with a mass consistent with the desired product. The reaction mixture was filtered and the filtrate was washed with methanol and dichloromethane. The solvents were removed under reduced pressure to provide an off-white powder. This material was recrystallized from acetonitrile to provide 0.11 g of N1,4-dimethyl-3-{3-[2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]propyl}-1-benzensulfonamide as a light yellow crystalline solid, m.p. 207-209° C.

Workup

  1. customno phenoxycarbonyl removal
  2. additionPalladium on carbon (0.1 g of 10%) was added
  3. waitthe reaction mixture was hydrogenated at 40 psi (2.8 Kg/cm2) for 8 hours
  4. customa small amount of phenoxycarbonyl removal
  5. additionPalladium black (0.1 g) was added
  6. waitthe reaction mixture was hydrogenated at 40 psi (2.8 Kg/cm2) for 16 hours
  7. filtrationThe reaction mixture was filtered
  8. washthe filtrate was washed with methanol and dichloromethane
  9. customThe solvents were removed under reduced pressure
  10. customto provide an off-white powder
  11. customThis material was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d07a429341de4138a962184ec4b5968c
Source dataset
uspto-grants-2004_01
Patent number
US06677348B2

Reaction notes

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