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Acetic Acid → N-[4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl) butyl]tetrahydro-2H-pyran-4-amine

HRID 1520414
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HRID 1520414 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.[O:25]1[CH2:30][CH2:29][C:28](=O)[CH2:27][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:28]2[CH2:29][CH2:30][O:25][CH2:26][CH2:27]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 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 223444144-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-amine

생성물 1

HCID 66896898N-[4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl) butyl]tetrahydro-2H-pyran-4-amine

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a suspension of 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-amine obtained in step VI of example I in tetrahydrofuran was added acetic acid (1 eq.) and tetrahydro-pyran-4-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 N-[4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]tetrahydro-2H-pyran-4-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-d1f1608422954e29b76e5b7b48cc1e5c
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073913B2

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