Hydrochloric Acid → 1-(3-aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 81884노트

반응식

HRID 81884 반응식
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:26][CH2:27][O:28][CH3:29])[N:14]([CH2:15][CH2:16][CH2:17][NH:18]C(=O)OC(C)(C)C)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl>O1CCOCC1>[NH2:18][CH2:17][CH2:16][CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[C:13]1[CH2:26][CH2:27][O:28][CH3:29]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 10318754Tert-butyl 3-(4-amino-2-(2-methoxyethyl)-1h-imidazo[4,5-c]quinolin-1-yl)propylcarbamate

생성물 1

HCID 223444281-(3-aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Tert-Butyl 3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate (5 g, U.S. Pat. No. 6,573,273, example 148) and hydrochloric acid in dioxane (100 mL of 4 M) were combined and stirred for 4 hours at ambient temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in methanol (30 mL). The pH was adjusted to pH 8 with 6 M sodium hydroxide. The solution was diluted with dichloromethane, ethyl acetate, triethylamine, and brine. The organic layer was concentrated under reduced pressure to provide an orange solid. This material was purified by prep HPLC (COMBIFLASH system eluting first with a gradient of 0 to 10% methanol in dichloromethane containing 1% ammonium hydroxide and then with a gradient of 9 to 30% methanol in dichloromethane containing 1% ammonium hydroxide) to provide 1.58 g of 1-(3-aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a yellow solid.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (30 mL)
  3. additionThe solution was diluted with dichloromethane, ethyl acetate, triethylamine, and brine
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customto provide an orange solid
  6. customThis material was purified by prep HPLC (COMBIFLASH system
  7. washeluting first with a gradient of 0 to 10% methanol in dichloromethane containing 1% ammonium hydroxide

출처 및 근거

ORD 기록
ord-21a5e11b2d44461f99acfde1a96cb6ac
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846710B2

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