Acetic Acid → [4-(2-Ethyl-imidazo[4,5-c]quinolin-1-yl)-butyl]-(tetrahydro-thiophen-3-yl)-amine

HRID 1520413

반응식

HRID 1520413 반응식
[CH2:1]([C:3]1[N:4]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1)[CH3:2].C(O)(=O)C.[S:25]1[CH2:29][CH2:28][C:27](=O)[CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[CH2:1]([C:3]1[N:4]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH:27]2[CH2:28][CH2:29][S:25][CH2:26]2)[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 61252Dihydro-3(2H)-thiophenoneHCID 5049666Sodium triacetoxyborohydrideHCID 223444144-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-amine

생성물 1

HCID 67145397[4-(2-Ethyl-imidazo[4,5-c]quinolin-1-yl)-butyl]-(tetrahydro-thiophen-3-yl)-amine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 4-(2-Ethyl-imidazo[4,5-c]quinolin-1-yl)-butylamine obtained in step VI in tetrahydrofuran was added acetic acid (1 eq.) and dihydrothiophen-3-one (1.1 eq.). Resulting reaction mixture was stirred for 10 min. Sodium triacetoxyborohydride (2.2 eq.) was added to reaction mixture over a period of 1 hrs and resulting suspension was then stirred for 4-5 hrs. Reaction was then quenched with methanol and concentrated to dryness. Reaction mixture was basified using aq.sodium hydroxide solution and extracted with chloroform. Organic layer was dried over sodium sulphate and concentrated under reduced pressure to yield sticky solid. Product was then purified by silica gel column chromatography to afford [4-(2-Ethyl-imidazo[4,5-c]quinolin-1-yl)-butyl]-(tetrahydro-thiophen-3-yl)-amine.

후처리

  1. customResulting
  2. customreaction mixture
  3. customresulting suspension
  4. stirringwas then stirred for 4-5 hrs
  5. customReaction
  6. customwas then quenched with methanol
  7. concentrationconcentrated to dryness
  8. customReaction mixture
  9. extractionsodium hydroxide solution and extracted with chloroform
  10. dry with materialOrganic layer was dried over sodium sulphate
  11. concentrationconcentrated under reduced pressure
  12. customto yield sticky solid
  13. customProduct was then purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-6f1b3722fa8345b99e62acad2e35e90a
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073913B2

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