Triethylamine → HCID 57475664, compound

HRID 1887430Notes

Reaction equation

HRID 1887430 reaction equation
C(N([CH2:6][CH3:7])CC)C.[F:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[CH2:14][CH2:15][O:16]2)=[CH:11][CH:10]=1.CS([Cl:24])(=O)=O.C(=O)(O)[O-].[Na+]>O1CCCC1>[Cl:24][C:13]1([CH:6]=[CH2:7])[C:12]2[C:17](=[CH:18][C:9]([F:8])=[CH:10][CH:11]=2)[O:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 146531327-fluoro-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 57475664HCID 57475664, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triethylamine (0.19 ml) was added to a solution of the compound 5-1 synthesized from 7-fluorochroman-4-one according to Example 4 (200 mg) in tetrahydrofuran (3.0 ml), cooled in an ice bath. A solution of methanesulfonyl chloride (177 mg) in tetrahydrofuran (2.0 ml) was added dropwise at the same temperature, followed by stirring for 1.5 hours. After confirming disappearance of the raw material, the reaction mixture was added to aqueous sodium bicarbonate to terminate the reaction. The aqueous layer was extracted with ethyl acetate. The aqueous layer was further extracted with ethyl acetate, and the combined organic layers were dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound (214 mg), which was used for the next reaction as a crude product.

Workup

  1. temperaturecooled in an ice bath
  2. customto terminate
  3. customthe reaction
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. extractionThe aqueous layer was further extracted with ethyl acetate
  6. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8f55cba370134d4c80dd899ddef70eab
Source dataset
uspto-grants-2013_08
Patent number
US08501733B2

Reaction notes

Loading…