Trichloroacetyl isocyanate → 8-benzyloxy-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 2383139노트

반응식

HRID 2383139 반응식
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N+:15]([O-])=[CH:14][C:13]3[N:20]=[CH:21][N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C([N:31]=C=O)=O.C[O-].[Na+]>>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[C:14]([NH2:31])[C:13]3[N:20]=[CH:21][N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 76400Trichloroacetyl isocyanate2회HCID 10942334Sodium MethoxideHCID 670510288-benzyloxy-1-(2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinoline

생성물 1

HCID 575453368-benzyloxy-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

실험 절차

A modification of the general method described in Part C of Example 3 was followed using 8-benzyloxy-1-(2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinoline (2.0 g, 5.8 mmol) as the starting material. The reaction with trichloroacetyl isocyanate was not complete after one hour as evidenced by a TLC analysis. Additional trichloroacetyl isocyanate (0.1 equivalent) was added, and the reaction was stirred for an additional hour. Following the reaction with sodium methoxide, the solid product was isolated by filtration and recrystallized from ethanol. The crystals were dried overnight in a vacuum oven at 45° C. to provide 1.6 g of 8-benzyloxy-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 214-216° C.

후처리

  1. customthe solid product was isolated by filtration
  2. customrecrystallized from ethanol
  3. customThe crystals were dried overnight in a vacuum oven at 45° C.

출처 및 근거

ORD 기록
ord-cdeba2a6568c48419974c845466aa849
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263594B2

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