Chloroform → 8-benzyloxy-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 2383133ノート

反応式

HRID 2383133 の反応式
C(Cl)(Cl)Cl.[CH2:5]([O:12][C:13]1[CH:22]=[CH:21][C:20]2[N+:19]([O-])=[CH:18][C:17]3[N:24]=[C:25]([CH2:28][CH3:29])[N:26]([CH3:27])[C:16]=3[C:15]=2[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.ClC(Cl)(Cl)C([N:34]=C=O)=O.C[O-].[Na+]>ClCCl.CO>[CH2:5]([O:12][C:13]1[CH:22]=[CH:21][C:20]2[N:19]=[C:18]([NH2:34])[C:17]3[N:24]=[C:25]([CH2:28][CH3:29])[N:26]([CH3:27])[C:16]=3[C:15]=2[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

7

反応物 4

HCID 6212Chloroform2 回HCID 76400Trichloroacetyl isocyanateHCID 10942334Sodium MethoxideHCID 670509858-benzyloxy-2-ethyl-1-methyl-5-oxido-1H-imidazo[4,5-c]quinoline

生成物 1

HCID 575453468-benzyloxy-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinolin-4-amine収率 73.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A modification of the general method of Part C of Example 3 was used. Chloroform (10 mL) was added to the solution of 8-benzyloxy-2-ethyl-1-methyl-5-oxido-1H-imidazo[4,5-c]quinoline (1.30 g, 3.90 mmol) in dichloromethane (35 mL) to improve the solubility. After the addition of trichloroacetyl isocyanate (0.633 mL, 5.31 mmol), the reaction was stirred for 3.5 hours. In the second step, chloroform (10 mL) was also added to the suspension in methanol (30 mL). After the reaction with sodium methoxide, the reaction was stirred over two nights, and the precipitate was isolated by filtration, washed with hexanes, recrystallized from methanol (278 mL/g), isolated by filtration, washed with hexanes, and dried for two days in a vacuum oven. A second crop of crystals from the mother liquor was combined with the first to provide 0.95 g of 8-benzyloxy-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinolin-4-amine as a white crystalline solid, mp 238.4-238.9° C.

後処理

  1. stirringthe reaction was stirred over two nights
  2. customthe precipitate was isolated by filtration
  3. washwashed with hexanes
  4. customrecrystallized from methanol (278 mL/g)
  5. customisolated by filtration
  6. washwashed with hexanes
  7. customdried for two days in a vacuum oven

出典と根拠

ORDレコード
ord-9bf6b813153d43f9a7d40a444b32f55e
出典データセット
uspto-grants-2012_09
特許番号
US08263594B2

反応ノート

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