Acetyl chloride → HCID 58833713, compound

HRID 2203556Notes

Reaction equation

HRID 2203556 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:30][O:31][CH2:32][CH3:33])[N:18]([CH2:19][C:20]([NH:23][C:24]([NH:26][CH:27]([CH3:29])[CH3:28])=[O:25])([CH3:22])[CH3:21])[C:14]=2[C:13]2[CH:12]=[CH:11][C:10]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH2:41])=[CH:9][C:8]=2[N:7]=1.C(N(CC)CC)C>ClCCl>[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:30][O:31][CH2:32][CH3:33])[N:18]([CH2:19][C:20]([NH:23][C:24]([NH:26][CH:27]([CH3:29])[CH3:28])=[O:25])([CH3:21])[CH3:22])[C:14]=2[C:13]2[CH:12]=[CH:11][C:10]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:1](=[O:3])[CH3:2])=[CH:9][C:8]=2[N:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 69507030HCID 69507030, compound

Product 1

HCID 58833713HCID 58833713, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (180 μL, 2.53 mmol) was added to a stirred solution of N-{2-[4-amino-7-[(6-aminohexyl)oxy]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N′-isopropylurea (prepared as described in Parts A-H of Example 369, 1.18 g, 2.30 mmol) and triethylamine (0.64 mL, 4.60 mmol) in dichloromethane (100 mL) at 0° C. After approximately 20 minutes, the solution was allowed to warm to room temperature and was stirred overnight. The solution was transferred to a separatory funnel and washed with water (2×). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, elution with 10% methanol in dichloromethane) to yield 0.34 g of N-(6-{[4-amino-2-(ethoxymethyl)-1-(2-{[(isopropylamino)carbonyl]amino}-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}hexyl)acetamide as a tan solid, mp 90-110° C.

Workup

  1. customThe solution was transferred to a separatory funnel
  2. washwashed with water (2×)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography (silica gel, elution with 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-63a12495d9ae4e3db2c9f7493ba90ed1
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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