1,1-Dichloroethane → HCID 57557308, compound

HRID 81943Notes

Reaction equation

HRID 81943 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][OH:21])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.ClC(Cl)C.[C:26](Cl)(=[O:28])[CH3:27]>N1C=CC=CC=1>[C:26]([O:21][CH2:20][C:13]1[N:14]([CH2:15][C:16]([OH:18])([CH3:17])[CH3:19])[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 6367Acetyl chlorideHCID 9817345O-Desethyl Resiquimod

Product 1

HCID 57557308HCID 57557308, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a round-bottomed flask with stir bar was added 1-(4-amino-2-hydroxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (1 g, 3.5 mmol) followed by dichloroethane (20 mL) and pyridine (3 mL). To the stirred suspension was added acetyl chloride (0.27 mL, 1.1 equivalents) and the reaction was stirred at ambient temperature for 30 min. The solvent was evaporated under reduced pressure to afford a solid. The product was isolated by two purifications by prep HPLC (ISCO Combiflash Separation System, Biotage Si 40+M column, eluted with a gradient of 0-7% methanol in dichloromethane with 1% ammonium hydroxide) to provide [4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate as an off white solid (130 mg), mp 203-205° C.; MS (ESI) m/z 329 (M+H); Anal. Calcd for C17H20N4O3.0.25CH4O: C, 61.59; H, 6.29; N, 16.66. Found C, 61.24; H, 6.22; N, 16.97.

Workup

  1. stirringthe reaction was stirred at ambient temperature for 30 min
  2. customThe solvent was evaporated under reduced pressure
  3. customto afford a solid
  4. customThe product was isolated by two purifications by prep HPLC (
  5. customISCO Combiflash Separation System, Biotage Si 40+M column
  6. washeluted with a gradient of 0-7% methanol in dichloromethane with 1% ammonium hydroxide)

Sources & evidence

ORD record
ord-d23cf62164bc4367aaacad1b5b0f406a
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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