Dimethylamine, hydrochloride → HCID 57657224, compound

HRID 244850Notes

Reaction equation

HRID 244850 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH3:22])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:23][CH2:24][C:25](O)=[O:26])=[CH:5][C:4]=2[N:3]=1.ON1C2C=CC=CC=2N=N1.[CH3:38][N:39](C)[CH2:40]CCN=C=NCC.Cl.CNC>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH3:22])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:23][CH2:24][C:25]([N:39]([CH3:40])[CH3:38])=[O:26])=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 69080290HCID 69080290, compound

Product 1

HCID 57657224HCID 57657224, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-[4-Amino-1-(2-hydroxy-2-methylpropyl)-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoic acid (1.25 g, 3.30 mmol), anhydrous pyridine (75 mL) and 1-hydroxybenzotriazole (892 mg, 6.60 mmol) were combined and the reaction was stirred for 30 minutes. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (1.27 g, 6.60 mmol) was added and the reaction mixture was stirred for an additional 15 minutes. Dimethylamine hydrochloride (540 mg, 6.60 mmol) was added in one portion and the reaction was stirred for an additional 4 hours. The solution was concentrated under reduced pressure and the resulting oil was dissolved in chloroform (50 mL) and washed with 1% aqueous sodium carbonate (3×25 mL). The combined aqueous washes were extracted with chloroform. The combined organic fractions were purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a CMA:chloroform gradient; 0-25% CMA over 1500 mL, followed by 25-30% CMA over 1000 mL) followed by recrystallization from acetonitrile to provide 931 mg of 3-[4-amino-1-(2-hydroxy-2-methylpropyl)-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylpropanamide as a white solid, mp 142-145° C.

Workup

  1. stirringthe reaction mixture was stirred for an additional 15 minutes
  2. stirringthe reaction was stirred for an additional 4 hours
  3. concentrationThe solution was concentrated under reduced pressure
  4. dissolutionthe resulting oil was dissolved in chloroform (50 mL)
  5. washwashed with 1% aqueous sodium carbonate (3×25 mL)
  6. extractionThe combined aqueous washes were extracted with chloroform
  7. customThe combined organic fractions were purified by chromatography
  8. washeluting with a CMA
  9. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-6d378ef58c54470996be84a107ea6bf6
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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