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

HRID 2383133노트

반응식

HRID 2383133 반응식
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

참가 물질

7

반응물 4

HCID 6212Chloroform2회HCID 76400Trichloroacetyl isocyanateHCID 10942334Sodium MethoxideHCID 670509858-benzyloxy-2-ethyl-1-methyl-5-oxido-1H-imidazo[4,5-c]quinoline

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9bf6b813153d43f9a7d40a444b32f55e
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263594B2

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