Triethylamine → HCID 57545329, compound

HRID 2383190Notes

Reaction equation

HRID 2383190 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:24])=[CH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:32][C:33]1[O:37][N:36]=[C:35]([C:38]2[S:39][CH:40]=[CH:41][CH:42]=2)[N:34]=1.C(N(CC)CC)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:18])([OH:19])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:24][CH2:32][C:33]3[O:37][N:36]=[C:35]([C:38]4[S:39][CH:40]=[CH:41][CH:42]=4)[N:34]=3)=[CH:5][C:4]=2[N:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 7368305-(chloromethyl)-3-(2-thienyl)-1,2,4-oxadiazoleHCID 1363405384-amino-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol

Product 1

HCID 57545329HCID 57545329, compoundYield 47.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

4-Amino-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol (100 mg, 0.3 mmol), cesium carbonate (195 mg, 0.6 mmol), 5-(chloromethyl)-3-(2-thienyl)-1,2,4-oxadiazole (71 mg, 0.33 mmol), tetrabutylammonium bromide (10 mg, 0.03 mmol), triethylamine (0.5 ml), and acetonitrile (10 mL) were combined and stirred at ambient temperature overnight. The reaction was concentrated under reduced pressure and dichloromethane was added to the residue. Undissolved solids were removed by filtration. The filtrate was concentrated under reduced pressure and subsequently purified by flash column chromatography on silica gel, eluting with a gradient of 0-5% methanol in dichloromethane. The clean fractions were combined and concentrated under reduced pressure. The solid was recrystallized from acetonitrile to yield 71 mg of 1-[4-amino-2-ethoxymethyl-7-[3-(thiophen-2-yl)-[1,2,4]oxadiazol-5-ylmethoxy]-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as a white solid, mp 173.0-175.0° C.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure and dichloromethane
  2. additionwas added to the residue
  3. customwere removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customsubsequently purified by flash column chromatography on silica gel
  6. washeluting with a gradient of 0-5% methanol in dichloromethane
  7. concentrationconcentrated under reduced pressure
  8. customThe solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-e5be11daa2ec43c0a160991944ae8b43
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

Loading…