Methanol → HCID 57657246, compound

HRID 244822Notes

Reaction equation

HRID 244822 reaction equation
CO.[NH2:3][C:4]1[C:13]2[N:14]=[CH:15][N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:12]=2[C:11]2[CH:10]=[C:9](/[CH:21]=[CH:22]/[CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][C:25]3=[O:29])[CH:8]=[CH:7][C:6]=2[N:5]=1>[Pd].C(O)C>[NH2:3][C:4]1[C:13]2[N:14]=[CH:15][N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:12]=2[C:11]2[CH:10]=[C:9]([CH2:21][CH2:22][CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][C:25]3=[O:29])[CH:8]=[CH:7][C:6]=2[N:5]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 69081423HCID 69081423, compound

Product 1

HCID 57657246HCID 57657246, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A glass Parr vessel was charged with 10% palladium on carbon catalyst (0.1 g), methanol (50 mL), ethanol (50 mL) and 1-{(2E)-3-[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]prop-2-enyl}pyrrolidin-2-one. The vessel was evacuated and charged with hydrogen gas (51 psi, 3.4×105 Pa). The reaction was shaken at ambient temperature overnight (approximately 18 hours). The reaction mixture was filtered to remove the catalyst and concentrated to dryness. The crude product was purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with 0-8% methanol in dichloromethane) followed by recrystallization from acetonitrile to yield 300 mg of 1-{3-[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]propyl}pyrrolidin-2-one as a white solid, mp 174-175° C.

Workup

  1. customThe vessel was evacuated
  2. additioncharged with hydrogen gas (51 psi, 3.4×105 Pa)
  3. filtrationThe reaction mixture was filtered
  4. customto remove the catalyst
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by chromatography
  7. washa HORIZON HPFC system (silica cartridge, eluting with 0-8% methanol in dichloromethane)
  8. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-aef8917b51c5460f86e870553e34d4af
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

Loading…