Pyridine, hydrofluoride (1:1) → HCID 22502712, compound

HRID 1251121Notes

Reaction equation

HRID 1251121 reaction equation
[CH2:1]([N:3](S(F)(F)F)[CH2:4][CH3:5])[CH3:2].[FH:10].[N:11]1[CH:16]=CC=CC=1.C(N1[CH2:24][CH2:23][N:22]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=[C:27]([C:35]3[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43]O)=CN=3)[N:26]=2)CC1)C>C(Cl)Cl>[CH2:1]([N:3]1[CH2:24][CH2:23][N:22]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=[C:27]([C:35]3[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43][F:10])=[N:11][CH:16]=3)[N:26]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 123472(Diethylamino)sulfur trifluorideHCID 22502662HCID 22502662, compound

Product 1

HCID 22502712HCID 22502712, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diethylaminosulfur trifluoride (53 ml) and pyridine hydrogen fluoride (320 ml) were dissolved in methylene chloride (3 ml), followed by the addition of 1-(1-ethylpiperazin-4-yl)-3-[5-(3-hydroxypropyl)pyridin-2-yl]isoquinoline (152 mg)/methylene chloride (2 ml) solution in nitrogen atmosphere at −70° C. After the cooling bath was removed, subsequently, the resulting mixture was stirred for 2 hr. The reaction solution was diluted with methylene chloride, washed sequentially with an aqueous solution of sodium bicarbonate and brine, dried (over MgSO4) and evaporated. The resulting residue was purified by (NH) silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a yellow oil (6 mg, yield; 5%).

Workup

  1. customAfter the cooling bath was removed
  2. additionThe reaction solution was diluted with methylene chloride
  3. washwashed sequentially with an aqueous solution of sodium bicarbonate and brine
  4. dry with materialdried (over MgSO4)
  5. customevaporated
  6. customThe resulting residue was purified by (NH) silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-21f977c6d0a74b13a1e185cabe2213fd
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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