Phenyl isocyanate → N-(2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N-phenylurea

HRID 430971노트

반응식

HRID 430971 반응식
N[CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[C:8]1[CH2:21][CH2:22][O:23][CH3:24].[C:25]1([N:31]=[C:32]=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC[N:36](CC)CC>C(Cl)Cl.CCOC(C)=O>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH2:21][CH2:22][O:23][CH3:24])[N:7]([CH2:6][CH2:5][O:4][CH2:3][CH2:2][N:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:32]([NH2:36])=[O:33])[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

참가 물질

6

반응물 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 121062041-[2-(2-Aminoethoxy)ethyl]-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

생성물 1

HCID 18762693N-(2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N-phenylurea수율 12.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

1-[2-(2-Aminoethoxy)ethyl]-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (750 mg, 2.28 mmol) was dissolved in 30 mL of anhydrous CH2Cl2 and cooled to 0° C. under N2. The reaction mixture was then treated with phenyl isocyanate (247 μL, 2.28 mmol) and Et3N (0.64 mL, 4.56 mmol) and allowed to warm slowly to room temperature. After stirring for 2 h, the reaction mixture was concentrated under reduced pressure to yield a yellow solid. The yellow solid was dissolved in a minimum amount of CH2Cl2 and EtOAc was added until the solution became turbid. The mixture was placed in a freezer overnight and white crystal formed. The crystals were isolated by filtration and were dried under vacuum to give 126 mg of N-(2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N-phenylurea. mp 171.0-174.0° C.;

후처리

  1. temperatureto warm slowly to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customto yield a yellow solid
  4. additionwas added until the solution
  5. waitThe mixture was placed in a freezer overnight
  6. customwhite crystal formed
  7. customThe crystals were isolated by filtration
  8. customwere dried under vacuum

출처 및 근거

ORD 기록
ord-872ef836817a43c6ad9da569a9738cfa
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06656938B2

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