Hydrochloric Acid → 1-(2-aminoethoxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 1845728ノート

反応式

HRID 1845728 の反応式
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([O:18][CH2:19][CH2:20][NH:21]C(=O)OC(C)(C)C)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].ClC1C=CC=C(C(OO)=O)C=1.[OH-].[NH4+:41].C1(S(Cl)(=O)=O)C=CC=CC=1.C(=O)(O)[O-].[Na+].Cl.[OH-].[Na+]>ClCCl.C(O)C.O>[NH2:21][CH2:20][CH2:19][O:18][N:6]1[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:41])[C:8]=2[N:17]=[C:5]1[CH2:4][O:3][CH2:1][CH3:2]

参加物

11

反応物 7

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 68926789tert-butyl 2-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]oxy}ethylcarbamate

生成物 1

HCID 689307621-(2-aminoethoxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒4 回

実験手順

To a stirred solution of tert-butyl 2-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]oxy}ethylcarbamate (6.0 g) from several batches of Part C in dichloromethane (100 mL) was added m-chloroperbenzoic acid (7.0 g). After about 2 hours, concentrated ammonium hydroxide (35 mL) and water (10 mL) were added. The mixture was cooled in an ice bath and a solution of benzenesulfonyl chloride (3.5 mL) in dichloromethane (25 mL) was added dropwise. The mixture was stirred for 2 hours at room temperature; then dichloromethane (75 mL) and saturated aqueous sodium bicarbonate (35 mL) were added. The aqueous layer was separated and extracted with dichloromethane (2×25 mL). The organic layers were combined, dried over potassium carbonate, filtered, and evaporated to afford an oil. The oil was dissolved in ethanol (50 mL). Concentrated hydrochloric acid (4 mL) was added and the mixture was heated at reflux for 2 days. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in methanol (10 mL) and added to stirred toluene (125 mL) causing an oil to form. The oil was stirred in dichloromethane (75 mL) and 15% sodium hydroxide solution (75 mL) for 2 hours. The layers were separated and the aqueous layer was extracted with dichloromethane (25 mL). The organic layers were combined, dried over potassium carbonate, filtered, and concentrated under reduced pressure to afford 1.3 g of 1-(2-aminoethoxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine.

後処理

  1. temperatureThe mixture was cooled in an ice bath
  2. customThe aqueous layer was separated
  3. extractionextracted with dichloromethane (2×25 mL)
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford an oil
  8. temperaturethe mixture was heated
  9. temperatureat reflux for 2 days
  10. concentrationThe reaction mixture was concentrated under reduced pressure
  11. dissolutionThe residue was dissolved in methanol (10 mL)
  12. additionadded
  13. stirringto stirred toluene (125 mL)
  14. customto form
  15. customThe layers were separated
  16. extractionthe aqueous layer was extracted with dichloromethane (25 mL)
  17. dry with materialdried over potassium carbonate
  18. filtrationfiltered
  19. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4292f85344564fc2891eb341232906bf
出典データセット
uspto-grants-2015_02
特許番号
US08951528B2

反応ノート

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