HCID 69082194, compound → HCID 57657236, compound

HRID 244853Notes

Reaction equation

HRID 244853 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH3:22])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH:23]=[CH:24][C:25]#[N:26])=[CH:5][C:4]=2[N:3]=1>[Pd].CO>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH3:22])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:23][CH2:24][C:25]#[N:26])=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 69082194HCID 69082194, compound

Product 1

HCID 57657236HCID 57657236, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A glass Parr vessel was charged with 10% palladium on carbon catalyst (200 mg), methanol (100 mL), and 3-[4-amino-1-(2-hydroxy-2-methylpropyl)-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enenitrile (925 mg, 2.63 mmol). The vessel was evacuated and charged with hydrogen gas (40 psi, 2.8×105 Pa). The mixture was shaken at 50° C. for approximately 18 hours. The reaction mixture was cooled to ambient temperature and then filtered through a 0.2 micron PTFE membrane filter. The filtrate was concentrated under reduced pressure and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a CMA:chloroform gradient; 0-25% CMA over 1500 mL, followed by 25-30% CMA over 500 mL) to provide 760 mg of 3-[4-amino-1-(2-hydroxy-2-methylpropyl)-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanenitrile as a white solid, mp 191-193° C.

Workup

  1. customThe vessel was evacuated
  2. additioncharged with hydrogen gas (40 psi, 2.8×105 Pa)
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. filtrationfiltered through a 0.2 micron PTFE membrane
  5. filtrationfilter
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by chromatography
  8. washeluting with a CMA

Sources & evidence

ORD record
ord-5c85f53672d74ec2aee035f4150a9f97
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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