ethyl (2E)-3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate → ethyl 3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoate

HRID 244885Notes

Reaction equation

HRID 244885 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][CH3:23])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6](/[CH:24]=[CH:25]/[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:5][C:4]=2[N:3]=1>[Pd].C(O)C>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][CH3:23])[N:14]([CH2:15][CH:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 57657271ethyl (2E)-3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate

Product 1

HCID 57657240ethyl 3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoateYield 83.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A glass Parr bottle was charged with 10% palladium on carbon (0.2 g) wetted with ethanol (10 mL) and a slurry of ethyl (2E)-3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate (1.81 g, 4.4 mmol) in ethanol (250 mL). The vessel was placed on a Parr apparatus, evacuated and charged with hydrogen (55 psi). The mixture was shaken at ambient temperature for 48 hours. The reaction mixture was filtered through a 0.2 micron PTFE membrane filter and the filter was rinsed with ethanol (300 ml). The filtrate was concentrated to dryness under reduced pressure. Recrystallization from acetonitrile provided 1.51 g of ethyl 3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoate as a white crystalline solid, mp 172-173° C.

Workup

  1. customevacuated
  2. additioncharged with hydrogen (55 psi)
  3. filtrationThe reaction mixture was filtered through a 0.2 micron PTFE membrane
  4. filtrationfilter
  5. washthe filter was rinsed with ethanol (300 ml)
  6. concentrationThe filtrate was concentrated to dryness under reduced pressure
  7. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-19c8f872a2554c9dae152e33978ae134
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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