Sodium Methoxide → HCID 19975235, compound

HRID 1450147Notes

Reaction equation

HRID 1450147 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[C:3]=1[NH:12][S:13]([C:16]1[N:26]=[C:19]2[C:20](Br)=[N:21][CH:22]=[C:23]([Br:24])[N:18]2[N:17]=1)(=[O:15])=[O:14].[CH3:27][O-:28].[Na+]>C(#N)C.CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[C:3]=1[NH:12][S:13]([C:16]1[N:26]=[C:19]2[C:20]([O:28][CH3:27])=[N:21][CH:22]=[C:23]([Br:24])[N:18]2[N:17]=1)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 19975225HCID 19975225, compound

Product 1

HCID 19975235HCID 19975235, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 686 mg (1.35 mmol) of N-(2-fluoro-6-methoxycarbonylphenyl)-5,8-dibromo[1,2,4]triazolo-[1,5-a]pyrazine-2-sulfonamide in 10 mL dry acetonitrile was treated with 3.0 mL (3.0 mmol) of a 1M solution of 15 sodium methoxide in dry methanol at 0° C. with stirring. The reaction was quenched after 5min with 0.5mL of glacial acetic acid and the volatiles were removed by evaporation under reduced pressure. The residue was triturated with water and the resulting light brown solid was collected by filtration and dried in a vacuum oven. This crude material was purified by flash column chromatography on silica gel using a 0.5 to 2percent ethanol/dichloromethane gradient as eluent to obtain 538 mg (87 percent of theory) of the title compound as a white glassy foam solid melting at 201°-202° C.

Workup

  1. customThe reaction was quenched after 5min with 0.5mL of glacial acetic acid
  2. customthe volatiles were removed by evaporation under reduced pressure
  3. customThe residue was triturated with water
  4. filtrationthe resulting light brown solid was collected by filtration
  5. customdried in a vacuum oven
  6. customThis crude material was purified by flash column chromatography on silica gel using a 0.5 to 2percent ethanol/dichloromethane gradient as eluent

Sources & evidence

ORD record
ord-5ba9f22a7d9c4831b1e3f355de748cd6
Source dataset
uspto-grants-1997_02
Patent number
US05602075

Reaction notes

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