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

HRID 62029Notes

Reaction equation

HRID 62029 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-99b707b6b8564314b67ee161e9b0a5f6
Source dataset
uspto-grants-2016_09
Patent number
US09446040B2

Reaction notes

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