Triethylamine → 4-[5-(6-Methanesulfonyloxymethyl-4-oxo-4H-pyran-3-yloxy)-pentyloxy]-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester

HRID 2108859Notes

Reaction equation

HRID 2108859 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[C:28](=[O:29])[CH:27]=[C:26]([CH2:30][OH:31])[O:25][CH:24]=1)=[CH:13][CH:12]=[C:11]([C:32]([F:35])([F:34])[F:33])[CH:10]=2)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[C:28](=[O:29])[CH:27]=[C:26]([CH2:30][O:31][S:44]([CH3:43])(=[O:46])=[O:45])[O:25][CH:24]=1)=[CH:13][CH:12]=[C:11]([C:32]([F:34])([F:33])[F:35])[CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57629444HCID 57629444, compound

Product 1

HCID 576294474-[5-(6-Methanesulfonyloxymethyl-4-oxo-4H-pyran-3-yloxy)-pentyloxy]-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[5-(6-hydroxymethyl-4-oxo-4H-pyran-3-yloxy)-pentyloxy]-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester 13 (330 mg, 0.67 mmol) in CH2Cl2 (15 mL) was added at 0° C. triethylamine (37 μL, 0.26 mmol), methanesulfonyl chloride (62 μL, 0.80 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=95:15. (5-(5-(6-(Trifluoromethyl)quinolin-4-yloxy)pentyloxy)-4-oxo-4H-pyran-2-yl)methylmethanesulfonate 18 was obtained (246 mg, 65% 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

Sources & evidence

ORD record
ord-f7616b12fa394a6f890e5b8989815b2e
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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