Thionyl Chloride → HCID 178499172, compound

HRID 1760180Notes

Reaction equation

HRID 1760180 reaction equation
S(Cl)(Cl)=O.[C:5]1([C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]3[NH:21][N:22]=[C:23]([C:24]([OH:26])=[O:25])[C:13]=3[N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:27](=O)([O-])O.[Na+]>CO>[C:5]1([C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]3[NH:21][N:22]=[C:23]([C:24]([O:26][CH3:27])=[O:25])[C:13]=3[N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 178524940HCID 178524940, compound

Product 1

HCID 178499172HCID 178499172, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

18 μL of thionyl chloride were initially introduced into 0.5 ml of methanol and the mixture was stirred for 30 min. 19 mg of 5-phenyl-1H-pyrazolo[4,3-c]isoquinoline-3-carboxylic acid (60) in 0.5 ml of methanol were then added dropwise. The mixture was stirred at RT for 12 h, after which a saturated solution of sodium hydrogen carbonate was added and the whole was extracted, in each case 1×, with ethyl acetate and methylene chloride. The organic phases were combined, dried over magnesium sulfate and concentrated under reduced pressure and the residue was purified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90). The following was obtained: 61. C18H13N3O2 (303.32) MS (ESI) 304 (M+H)

Workup

  1. stirringThe mixture was stirred at RT for 12 h
  2. extractionthe whole was extracted, in each case 1×, with ethyl acetate and methylene chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)
  6. customThe following was obtained

Sources & evidence

ORD record
ord-904c219816fa49c3a021f7b0fdf426d9
Source dataset
uspto-grants-2005_01
Patent number
US06841556B2

Reaction notes

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