Triethylamine → HCID 86657934, compound

HRID 1186321Notes

Reaction equation

HRID 1186321 reaction equation
Cl.[Cl:2][C:3]1[C:12]([O:13][CH:14]([C:19]2(F)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:15]([F:18])([F:17])[F:16])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35].[C:38](=O)(O)[O-].[Na+]>ClCCl>[Cl:2][C:3]1[C:12]([O:13][CH:14]([C:19]2([CH3:38])[CH2:24][CH2:23][N:22]([S:34]([CH3:33])(=[O:36])=[O:35])[CH2:21][CH2:20]2)[C:15]([F:18])([F:17])[F:16])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86657931HCID 86657931, compound

Product 1

HCID 86657934HCID 86657934, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Chloro-3-[2,2,2-trifluoro-1-(4-fluoropiperidin-4-yl)-ethoxy]quinoxaline hydrochloride (157 mg, 0.396 mmol) was dissolved in dichloromethane (3.0 mL). To this, triethylamine (0.197 mL, 1.19 mmol) and methanesulfonyl chloride (0.0459 mL, 0.594 mmol) were successively added and the mixture was stirred at room temperature for 1 hour. The reaction was stopped by addition of a saturated aqueous sodium bicarbonate solution to the reaction mixture, and extraction with dichloromethane was performed, followed by drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3) to give Compound BAI (146 mg, yield: 84%).

Workup

  1. dry with materialby drying over anhydrous sodium sulfate
  2. customThe solvent was evaporated off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)
  4. customto give Compound BAI (146 mg, yield: 84%)

Sources & evidence

ORD record
ord-abad312306f640c8829de8b71cb54332
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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