Sodium Thiosulfate → HCID 89812859, compound

HRID 1481205Notes

Reaction equation

HRID 1481205 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([C:26]#[N:27])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13](SC1CCCCC1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[CH:28]1[CH:33]=[C:32](Cl)[CH:31]=[C:30](C(OO)=O)[CH:29]=1.[O-:39][S:40]([O-:43])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([C:26]#[N:27])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([S:40]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)(=[O:43])=[O:39])[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 89812884HCID 89812884, compound

Product 1

HCID 89812859HCID 89812859, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-cyano-7-cyclohexylsulfanyl-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (325 mg, 0.85 mmol) and mCPBA (526 mg, 3.05 mmol) in CH2Cl2 was stirred at room temperature overnight. The reaction was quenched by adding Na2S2O3 (3.6 equivalents). It was then filtered and rinsed with CH2Cl2. Filtrate was concentrated and purified by silica gel chromatography, eluting with 10-100% EtOAc/hexanes to provide the title compound 297 mg (0.71 mmol) in 84% yield. LC-MS ESI−: 414.99 (M−1)−.

Workup

  1. customThe reaction was quenched
  2. filtrationIt was then filtered
  3. washrinsed with CH2Cl2
  4. concentrationFiltrate was concentrated
  5. custompurified by silica gel chromatography
  6. washeluting with 10-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-365f27c3e3724cf0a980904a67d7be0e
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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