Sulfuric Acid → HCID 135870696, compound

HRID 1050780Notes

Reaction equation

HRID 1050780 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[C:12]([C:25]#[CH:26])[N:13]=[C:14]([C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])[C:15]=3[OH:17])[S:10][N:9]=2)=[CH:4][CH:3]=1.[OH:27]S(O)(=O)=O>O>[C:25]([C:12]1[N:13]=[C:14]([C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])[C:15]([OH:17])=[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:9][S:10][C:11]=12)(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 135870681HCID 135870681, compound

Product 1

HCID 135870696HCID 135870696, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the solution of {[3-(4-chloro-phenyl)-7-ethynyl-4-hydroxy-isothiazolo[5,4-c]pyridine-5-carbonyl]-amino}-acetic acid (0.28 mmol) in actone/water=4:1 (2.8 mL) was added conc. H2SO4 (36.2 mg, 0.37 mmol) and HgSO4 (84.3 mg, 0.28 mmol). The reaction mixture was refluxed for 2 h. After cooling to r.t. the mixture was concentrated in vacuo. The residue was dissolved in DMSO (2.5 mL) and purified by flash column chromatography on C18 (40 g), eluting with 30-80% CH3CN/H2O in 0.1% HCOOH to give the title compound (26 mg) as a brown solid: MS (m/z) 406.0 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was dissolved in DMSO (2.5 mL)
  4. custompurified by flash column chromatography on C18 (40 g)
  5. washeluting with 30-80% CH3CN/H2O in 0.1% HCOOH

Sources & evidence

ORD record
ord-6e047d48faa74642a3483e261a3f48a8
Source dataset
uspto-grants-2016_07
Patent number
US09387200B2

Reaction notes

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