Acetyl chloride → HCID 58833713、化合物

HRID 2203556ノート

反応式

HRID 2203556 の反応式
[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

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 69507030HCID 69507030、化合物

生成物 1

HCID 58833713HCID 58833713、化合物収率 26.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-63a12495d9ae4e3db2c9f7493ba90ed1
出典データセット
uspto-grants-2016_06
特許番号
US09365567B2

反応ノート

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