Ammonia → 1-(4-Amino-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

HRID 991926노트

반응식

HRID 991926 반응식
Cl[C:2]1[C:11]([NH:12][C:13](=O)[CH2:14]COC)=[C:10]([NH:19][CH2:20][C:21]([OH:24])([CH3:23])[CH3:22])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH3:25].[CH3:26][OH:27]>O.C(=O)(O)[O-].[Na+]>[NH2:25][C:2]1[C:11]2[N:12]=[C:13]([CH2:14][O:27][CH3:26])[N:19]([CH2:20][C:21]([CH3:22])([CH3:23])[OH:24])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

참가 물질

6

반응물 3

HCID 222AmmoniaHCID 887MethanolHCID 22672655N-[2-Chloro-4-(2-hydroxy-2-methylpropyl)amino-3-quinolinyl]-3-methoxypropanamide

생성물 1

HCID 100861791-(4-Amino-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

시약·촉매·용매 2

HCID 962Water용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
150 °C

실험 절차

N-[2Chloro-4-(2-hydroxy-2-methylpropyl)amino-3-quinolinyl]-3-methoxypropanamide (6 g, Example 110) was added to 5% ammonia in methanol (60 mL). The mixture was heated in a Parr bomb for 5 hours at approximately 150° C. The solvent was evaporated under vacuum to give a brown residue. The residue was diluted with water and sodium bicarbonate then extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over magnesium sulfate then evaporated to provide a tan solid. The solid was purified by silica gel chromatography to provide 1.64 g of the desired product as a solid, m.p. 174-175° C. Analysis: Calculated: %C, 65.0; %H, 7.0; %N, 17.8; Found: %C, 64.8; %H, 7.0; %N, 17.7.

후처리

  1. customThe solvent was evaporated under vacuum
  2. customto give a brown residue
  3. extractionthen extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. customthen evaporated
  8. customto provide a tan solid
  9. customThe solid was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-e359be261c9c4b048756c94030a032aa
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06465654B2

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