Triethylamine → (5-(5-(8-(Trifluoromethyl)quinolin-4-yloxy)pentyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate

HRID 2108860Notes

Reaction equation

HRID 2108860 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:21](=[O:28])[CH:22]=[C:23]([CH2:26][OH:27])[O:24][CH:25]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[CH3:38][S:39]([O:27][CH2:26][C:23]1[O:24][CH:25]=[C:20]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][O:13][C:8]2[C:7]3[C:12](=[C:3]([C:2]([F:1])([F:29])[F:30])[CH:4]=[CH:5][CH:6]=3)[N:11]=[CH:10][CH:9]=2)[C:21](=[O:28])[CH:22]=1)(=[O:41])=[O:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 179758355-(5-(8-(Trifluoromethyl)quinolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

Product 1

HCID 57629440(5-(5-(8-(Trifluoromethyl)quinolin-4-yloxy)pentyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonateYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(5-(8-(trifluoromethyl)quinolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one 14 (430 mg, 1.02 mmol) in CH2Cl2 (15 mL) was added at 0° C. triethylamine (173 μL, 1.21 mmol), methanesulfonyl chloride (95 μL, 1.21 mmol). The solution was stirred at RT for 1 h. Dichloromethane (50 mL) was added and the solution was washed with water (2×100 mL), dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography on silica using as eluent (CH2Cl2:MeOH)=95:05. (5-(5-(8-(Trifluoromethyl)quinolin-4-yloxy)pentyloxy-4-oxo-4H-pyran-2-yl)methyl methanesulfonate 19 was obtained (188 mg, 37% yield) as a pale yellow oil.

Workup

  1. washthe solution was washed with water (2×100 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by column chromatography on silica using as eluent (CH2Cl2:MeOH)=95:05

Sources & evidence

ORD record
ord-5f57c61259194e2c91c8b09dd5a34878
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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