Benzenesulfonyl chloride → methyl [4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]carbamate

HRID 1097610노트

반응식

HRID 1097610 반응식
[OH:1][C:2]([CH3:24])([CH3:23])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N+:9]([O-])=[CH:8][C:7]=2[N:6]=[C:5]1[NH:18][C:19](=[O:22])[O:20][CH3:21].[OH-].[NH4+:26].C1(S(Cl)(=O)=O)C=CC=CC=1>CO>[NH2:26][C:8]1[C:7]2[N:6]=[C:5]([NH:18][C:19](=[O:22])[O:20][CH3:21])[N:4]([CH2:3][C:2]([OH:1])([CH3:24])[CH3:23])[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

참가 물질

5

반응물 3

HCID 7369Benzenesulfonyl chloride2회HCID 14923Ammonium HydroxideHCID 86626309methyl [1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]carbamate

생성물 1

HCID 57550537methyl [4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]carbamate수율 45.5%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

A suspension of methyl [1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]carbamate (0.80 g, 2.4 mmol) in methanol (10 mL) was stirred vigorously and cooled to 0° C. Concentrated ammonium hydroxide (0.8 mL, 25 mmol) was added followed by benzenesulfonyl chloride (0.9 g, 5 mmol), which was added dropwise. The mixture was stirred for two hours at 0° C. to 5° C. An analysis by LC/MS indicated the reaction was incomplete. Additional benzenesulfonyl chloride (0.9 g) was added, and the reaction mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure, and the residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 0% to 25% CMA in chloroform) followed by recrystallization from ethyl acetate to provide 0.36 g of methyl [4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]carbamate as a white solid, mp 255-258° C. (decomposition).

후처리

  1. additionwas added dropwise
  2. stirringThe mixture was stirred for two hours at 0° C. to 5° C
  3. stirringthe reaction mixture was stirred overnight at room temperature
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 0% to 25% CMA in chloroform)
  6. customfollowed by recrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-e5d65f421c004249bd3844edb1cfded0
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143270B2

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