Hydrochloric Acid → Methyl 4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline-7-carboxylate

HRID 63703Notes

Reaction equation

HRID 63703 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]1[N:16]([CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[C:15]([CH2:22][O:23][CH2:24][CH3:25])=[N:14][C:13]=1[C:26]#[N:27])[C:5]([O:7][CH3:8])=[O:6].Cl.O1CCOCC1>C(OCC)(=O)C>[NH2:27][C:26]1[C:13]2[N:14]=[C:15]([CH2:22][O:23][CH2:24][CH3:25])[N:16]([CH2:17][C:18]([OH:21])([CH3:19])[CH3:20])[C:12]=2[C:11]2[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118451573HCID 118451573, compound

Product 1

HCID 118451553Methyl 4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline-7-carboxylateYield 109.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 3-amino-4-(4-cyano-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazol-5-yl)benzoate (2.79 g, 7.49 mmol) was combined with a solution of HCl in dioxane (4M, 56.2 mL, 225 mmol) to give an orange solution. The reaction mixture was heated to 90° C. under argon with stirring. After 1 h at 90° C. the mixture was cooled to room temperature and concentrated in vacuo to obtain a beige solid. The solid was dissolved in ethyl acetate (500 mL) washed with a mixture of water (100 mL) and saturated sodium bicarbonate solution (250 mL). The water phase was extracted with ethyl acetate (2×250 mL), organic phases were combined, dried with MgSO4 and concentrated in vacuo to obtain a yellow solid (3.05 g). The solid material was re-crystallized from ethyl acetate/heptane to give the title compound (2.4 g, 86%) as light yellow solid; LC-MS (UV peak area, ESI) 99%, 373.1884 (MH+).

Workup

  1. customto give an orange solution
  2. temperatureAfter 1 h at 90° C. the mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customto obtain a beige solid
  5. washwashed with a mixture of water (100 mL) and saturated sodium bicarbonate solution (250 mL)
  6. extractionThe water phase was extracted with ethyl acetate (2×250 mL), organic phases
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bdc38a4e10a54ac6ba4c2dac1b458cbc
Source dataset
uspto-grants-2016_09
Patent number
US09447097B2

Reaction notes

Loading…