HCID 67051030, compound → HCID 136347853, compound

HRID 540905Notes

Reaction equation

HRID 540905 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][N:26]4[CH2:30][CH2:29][CH2:28][S:27]4(=[O:32])=[O:31])[C:20]([CH2:33][O:34][CH2:35][CH3:36])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1>C(#N)C.CO.[OH-].[Pd+2].[OH-]>[O:32]=[S:27]1(=[O:31])[CH2:28][CH2:29][CH2:30][N:26]1[CH2:25][CH2:24][CH2:23][CH2:22][N:21]1[C:13]2[C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:19]=[C:20]1[CH2:33][O:34][CH2:35][CH3:36]

Participants

5

Reactant 1

HCID 67051030HCID 67051030, compound

Product 1

HCID 136347853HCID 136347853, compoundYield 58.1%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 7-(benzyloxy)-1-[4-(1,1-dioxidoisothiazolidin-2-yl)butyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline (4.6 g, 9.04 mmol) and palladium hydroxide (1.5 g) in acetonitrile (50 mL) and methanol (75 mL) was hydrogenated on a Parr apparatus at 50 psi (3.5×105 Pa) for 28 hours. The mixture was filtered through CELITE filter agent, which was rinsed afterwards with 40% methanol in acetonitrile (600 mL). The filtrates were combined and concentrated under reduced pressure to yield a yellow solid that was triturated with acetonitrile and isolated by filtration to afford 2.2 g of 1-[4-(1,1-dioxidoisothiazolidin-2-yl)butyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-ol as a pale yellow powder.

Workup

  1. filtrationThe mixture was filtered through CELITE
  2. filtrationfilter agent, which
  3. washwas rinsed afterwards with 40% methanol in acetonitrile (600 mL)
  4. concentrationconcentrated under reduced pressure
  5. customto yield a yellow solid
  6. customthat was triturated with acetonitrile
  7. customisolated by filtration

Sources & evidence

ORD record
ord-fd1b3e113bb04600bd97f1a6cf5ffd7b
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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