Sodium Carbonate → N-{3-[4-amino-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-yloxy]propyl}-2-methylpropanamide

HRID 540828노트

반응식

HRID 540828 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:19]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:18]([CH2:24][CH2:25][CH3:26])=[N:17][C:11]=3[C:12]([NH2:16])=[N:13][C:14]=2[CH:15]=1.[C:27](Cl)(=[O:31])[CH:28]([CH3:30])[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[NH2:16][C:12]1[C:11]2[N:17]=[C:18]([CH2:24][CH2:25][CH3:26])[N:19]([CH2:20][CH:21]([CH3:22])[CH3:23])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:1][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])=[CH:15][C:14]=2[N:13]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 62325Isobutyryl chlorideHCID 588337127-(3-aminopropoxy)-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

생성물 1

HCID 11270234N-{3-[4-amino-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-yloxy]propyl}-2-methylpropanamide수율 75.5%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

A solution of 7-(3-aminopropoxy)-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (0.500 g, 1.41 mmol) in chloroform (15 mL) was cooled to 0° C. Isobutyryl chloride (0.147 mL, 1.40 mmol) was added dropwise, and the reaction was stirred for 30 minutes. The reaction was diluted with chloroform and poured into 3% aqueous sodium carbonate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting white solid was recrystallized from acetonitrile to yield 0.450 g of N-{3-[4-amino-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-yloxy]propyl}-2-methylpropanamide as feathery, white crystals, mp 179-181° C.

후처리

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting white solid was recrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-c86be1991436446f9b51f5ff59491c8b
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871782B2

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