Triethylamine → (5-(5-(7-(Trifluoromethyl)quinolin-4-yloxy)pentyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate

HRID 2108858Notes

Reaction equation

HRID 2108858 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[C:21](=[O:28])[CH:22]=[C:23]([CH2:26][OH:27])[O:24][CH:25]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=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:7]2[C:6]3[C:11](=[CH:12][C:3]([C:2]([F:1])([F:29])[F:30])=[CH:4][CH:5]=3)[N:10]=[CH:9][CH:8]=2)[C:21](=[O:28])[CH:22]=1)(=[O:41])=[O:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 17975832HCID 17975832, compound

Product 1

HCID 86607092(5-(5-(7-(Trifluoromethyl)quinolin-4-yloxy)pentyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(5-(7-(trifluoromethyl)quinolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one 12 (240 mg, 0.57 mmol) in CH2Cl2 (15 mL) was added at 0° C. triethylamine (96 μL, 0.68 mmol), methanesulfonyl chloride (53 μL, 0.68 mmol). The solution was stirred at RT for 1.5 h. Dichloromethane (50 mL) was added and the solution was washed with water (3×100 mL), dried over MgSO4, filtered and evaporated. (5-(5-(7-(trifluoromethyl)quinolin-4-yloxy)pentyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate 17 was obtained (260 mg, 91% yield) as a crude yellow oil.

Workup

  1. washthe solution was washed with water (3×100 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-ca40892216344579a3d03685fe509abd
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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