Triethylamine → HCID 12149142, compound

HRID 2108846Notes

Reaction equation

HRID 2108846 reaction equation
[OH:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][S:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([C:27]([F:30])([F:29])[F:28])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[C:7](=[O:9])[CH:8]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[O:9]=[C:7]1[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][S:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([C:27]([F:30])([F:29])[F:28])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)=[CH:5][O:4][C:3]([CH2:2][O:1][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10433304HCID 10433304, compound

Product 1

HCID 12149142HCID 12149142, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-hydroxymethyl-5-[5-(7-trifluoromethyl-quinolin-4-ylsulfanyl)-pentyloxy]-4H-pyran-4-one EHT 5909 (0.10 g, 0.23 mmol) in 4 mL of dichloromethane at 5° C. were added triethylamine (35 μl, 0.25 mmol) and methanesulfonyl chloride (19.4 μl, 0.25 mmol). The reaction mixture was stirred 18 h at room temperature. Dichloromethane (20 mL) was added and the solution was washed with aqueous NaHCO3 10% (2×30 mL). The organic layer was dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified by chromatography on silica using as eluent CH2Cl2:MeOH=98:2. After evaporation methanesulfonic acid 4-oxo-5-[6-(7-trifluoromethyl-quinolin-4-ylsulfanyl)-hexyloxy]-4H-pyran-2-ylmethyl ester 9 (83 mg, 69%) was obtained as a white solid.

Workup

  1. washthe solution was washed with aqueous NaHCO3 10% (2×30 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude product was purified by chromatography on silica using as eluent CH2Cl2
  6. customAfter evaporation methanesulfonic acid 4-oxo-5-[6-(7-trifluoromethyl-quinolin-4-ylsulfanyl)-hexyloxy]-4H-pyran-2-ylmethyl ester 9 (83 mg, 69%)
  7. customwas obtained as a white solid

Sources & evidence

ORD record
ord-46531b24d8b44f3f9a54dc04c01f03e5
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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