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

HRID 81884ノート

反応式

HRID 81884 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-21a5e11b2d44461f99acfde1a96cb6ac
出典データセット
uspto-grants-2014_09
特許番号
US08846710B2

反応ノート

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