Methyl Acrylate → HCID 57657222, compound

HRID 244823Notes

Reaction equation

HRID 244823 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[NH2:30][C:31]1[C:40]2[N:41]=[C:42]([CH2:49][O:50][CH2:51][CH3:52])[N:43]([CH2:44][C:45]([CH3:48])([OH:47])[CH3:46])[C:39]=2[C:38]2[CH:37]=[CH:36][C:35](Br)=[CH:34][C:33]=2[N:32]=1.[C:54]([O:58][CH3:59])(=[O:57])[CH:55]=[CH2:56]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:30][C:31]1[C:40]2[N:41]=[C:42]([CH2:49][O:50][CH2:51][CH3:52])[N:43]([CH2:44][C:45]([OH:47])([CH3:48])[CH3:46])[C:39]=2[C:38]2[CH:37]=[CH:36][C:35](/[CH:56]=[CH:55]/[C:54]([O:58][CH3:59])=[O:57])=[CH:34][C:33]=2[N:32]=1

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 219842117-bromo-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 57657222HCID 57657222, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

A thick walled glass reaction vessel was charged with anhydrous DMF (2 mL), palladium (II) Acetate (0.01 equivalents (eq)), tri-o-tolylphosphine (0.02 eq) and triethylamine (3 eq). To this orange solution was added a solution of 1-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol in 50 mL anhydrous DMF followed by the addition of methyl acrylate (1.0 eq). The reaction mixture was purged with nitrogen, sealed and heated at 120° C. overnight, and slowly cooled to room temperature. The reaction mixture was concentrated to dryness and then slurried in water (50 mL). Saturated potassium carbonate solution (25 mL) was added. The mixture was extracted with dichloromethane (4×50 mL). The combined extracts were concentrated under reduced pressure and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with 0-25% CMA in chloroform) to provide Methyl(2E)-3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate as a white solid.

Workup

  1. customA thick walled glass reaction vessel
  2. customThe reaction mixture was purged with nitrogen
  3. customsealed
  4. temperatureslowly cooled to room temperature
  5. concentrationThe reaction mixture was concentrated to dryness
  6. additionSaturated potassium carbonate solution (25 mL) was added
  7. extractionThe mixture was extracted with dichloromethane (4×50 mL)
  8. concentrationThe combined extracts were concentrated under reduced pressure
  9. custompurified by chromatography
  10. washa HORIZON HPFC system (silica cartridge, eluting with 0-25% CMA in chloroform)

Sources & evidence

ORD record
ord-a7145933cd4246dd876ebe6554d63e17
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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