Benzenesulfonyl chloride → 5-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide

HRID 2366707노트

반응식

HRID 2366707 반응식
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH2:24])=[O:23])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.C1(S(Cl)(=O)=O)C=CC=CC=1.[OH-].[NH4+:47]>>[NH2:47][C:9]1[C:8]2[N:17]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH2:24])=[O:23])[C:7]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

참가 물질

5

반응물 4

HCID 7369Benzenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 574470925-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide

생성물 1

HCID 574470905-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide

실험 절차

5-[2-(Ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide (2.25 g, 6.89 mmol) was treated with mCPBA (2.77 g, 12.0 mmol), ammonium hydroxide (40 mL), and benzenesulfonyl chloride (1.71 mL, 13.4 mmol) according to the method described in Part D of Example 36. The crude product was purified by column chromatography on silica gel (eluting with dichloromethane:methanol in a gradient from 90:10 to 85:15). The resulting product was triturated with 10% aqueous sodium hydroxide, isolated by filtration, washed with water, and dried overnight in a vacuum oven to provide 0.752 g of 5-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide as a tan solid, mp 198-200° C.

후처리

  1. customThe crude product was purified by column chromatography on silica gel (
  2. washeluting with dichloromethane
  3. customThe resulting product was triturated with 10% aqueous sodium hydroxide
  4. customisolated by filtration
  5. washwashed with water
  6. customdried overnight in a vacuum oven

출처 및 근거

ORD 기록
ord-1fb0899b8c3b4397bcb240056112d596
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697873B2

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