Sulfuric Acid → HCID 135870696, compound

HRID 1847253Notes

Reaction equation

HRID 1847253 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-b60eb6f9cc154311b77c5649b586df15
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

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