Chloromethyl ethyl ether → HCID 66652550, compound

HRID 2283631Notes

Reaction equation

HRID 2283631 reaction equation
[Cl:1][C:2]1[C:3]([F:20])=[CH:4][C:5]([F:19])=[C:6]([S:8]([NH:11][C:12]2[N:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.C(N(CC)C(C)C)(C)C.[CH2:30]([O:32][CH2:33]Cl)[CH3:31]>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([F:20])=[CH:4][C:5]([F:19])=[C:6]([S:8]([N:11]([CH2:33][O:32][CH2:30][CH3:31])[C:12]2[N:13]=[CH:14][C:15]([F:18])=[CH:16][N:17]=2)(=[O:10])=[O:9])[CH:7]=1

Participants

6

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 81531DiisopropylethylamineHCID 66653104HCID 66653104, compound

Product 1

HCID 66652550HCID 66652550, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-2,4-difluoro-N-(5-fluoropyrimidin-2-yl)benzenesulfonamide (Preparation 12, 0.28 g, 0.86 mmol) in dichloromethane (7 mL) at 0° C. was added N,N-diisopropylethylamine (0.23 mL, 1.32 mmol) and chloromethyl ethyl ether (0.088 mL, 0.95 mmol). The reaction mixture was stirred for 20 hours allowing the solution to gradually warm to ambient temperature. The reaction mixture was diluted with ethyl acetate, washed with 1N aqueous sodium hydroxide solution, water, and brine and then dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexanes to ethyl acetate gradient elution) to afford the title compound as a white solid (173 mg).

Workup

  1. washwashed with 1N aqueous sodium hydroxide solution, water, and brine
  2. dry with materialdried over anhydrous sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (hexanes to ethyl acetate gradient elution)

Sources & evidence

ORD record
ord-17bd9d6ed0664b5c90ebfc94b32c4f4f
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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