Potassium Hydroxide → HCID 58970366, compound

HRID 2366745Notes

Reaction equation

HRID 2366745 reaction equation
B(Br)(Br)Br.[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:26][O:27]CC)[N:18]([CH2:19][C:20]([CH3:25])([CH3:24])[C:21]([NH2:23])=[O:22])[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1.[OH-].[K+]>ClCCl.ClCCCl.CO>[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:26][OH:27])[N:18]([CH2:19][C:20]([CH3:25])([CH3:24])[C:21]([NH2:23])=[O:22])[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 25134Boron tribromideHCID 57447059HCID 57447059, compound

Product 1

HCID 58970366HCID 58970366, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Boron tribromide (15 mL of a 1 N solution in dichloromethane) was added to a solution of 3-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanamide (1.1 g, 3.2 mmol, Example 28) in 1,2-dichloroethane (35 mL). The reaction was heated at reflux for 35 minutes, cooled to approximately 0° C., and adjusted to pH 8 with the addition of a solution of potassium hydroxide (90 mL of a 0.5 N solution in methanol). The volatiles were removed under reduced pressure, and the residue was mixed with methanol (50 mL) and isolated by filtration. The filtrate was concentrated under reduced pressure, and the residue was stirred overnight with saturated aqueous sodium bicarbonate (35 mL). The resulting solid was isolated by filtration, combined with material from another run, and purified by column chromatography on silica gel (eluting with 20% methanol in dichloromethane containing 1% ammonium hydroxide) and dried in a vacuum oven for three hours at 60° C. to provide 3-[4-amino-2-(hydroxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanamide as white crystals, mp 201-203° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 35 minutes
  3. customThe volatiles were removed under reduced pressure
  4. additionthe residue was mixed with methanol (50 mL)
  5. customisolated by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe resulting solid was isolated by filtration
  8. custompurified by column chromatography on silica gel (eluting with 20% methanol in dichloromethane containing 1% ammonium hydroxide)
  9. customdried in a vacuum oven for three hours at 60° C.

Sources & evidence

ORD record
ord-4f970b36d0e54127a48e68170dafd832
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…