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

HRID 1520413ノート

反応式

HRID 1520413 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6f1b3722fa8345b99e62acad2e35e90a
出典データセット
uspto-grants-2015_07
特許番号
US09073913B2

反応ノート

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