Water → HCID 59130466, compound

HRID 1992620Notes

Reaction equation

HRID 1992620 reaction equation
[NH2:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[CH:8]1.C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29].O>N1C=CC=CC=1>[NH2:20][C:11]1[C:10]2[N:9]=[CH:8][N:7]([CH2:6][CH2:5][CH2:4][CH2:3][O:2][NH:1][C:28](=[O:30])[CH3:29])[C:19]=2[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 68539374HCID 68539374, compound

Product 1

HCID 59130466HCID 59130466, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the 1-[4-(aminooxy)butyl]-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine from Part C (200 mg, 0.73 mmol) and triethylamine (512 μL, 3.56 mmol) in pyridine (25 mL) was added acetyl chloride (57 μL, 0.80 mmol). The solution was stirred for 30 minutes at ambient temperature, and additional acetyl chloride (1 equivalent) was added. After 1 hour, water was added and the mixture was extracted with dichloromethane (2×). The aqueous layer was concentrated under reduced pressure to yield a white solid that was purified by chromatography (silica gel, gradient elution with 0-10% methanol in dichloromethane with a small amount of concentrated ammonium hydroxide added) to provide 30 mg of N-[4-(4-amino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butoxy]acetamide as a white solid.

Workup

  1. waitAfter 1 hour
  2. extractionthe mixture was extracted with dichloromethane (2×)
  3. concentrationThe aqueous layer was concentrated under reduced pressure
  4. customto yield a white solid
  5. customthat was purified by chromatography (
  6. washsilica gel, gradient elution with 0-10% methanol in dichloromethane with a small amount of concentrated ammonium hydroxide
  7. additionadded)

Sources & evidence

ORD record
ord-0d0f6640ff1a4a359dc6ab4089431475
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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