Methanol → HCID 86711612, compound

HRID 527344Notes

Reaction equation

HRID 527344 reaction equation
[CH3:1][C:2]1[N:7]([C:8]2[N:9]([CH3:13])[N:10]=[CH:11][CH:12]=2)[CH:6]=[C:5]([C:14]([OH:16])=[O:15])[C:4](=[O:17])[CH:3]=1.S(Cl)(Cl)=O.[CH3:22]O>>[CH3:22][O:15][C:14]([C:5]1[C:4](=[O:17])[CH:3]=[C:2]([CH3:1])[N:7]([C:8]2[N:9]([CH3:13])[N:10]=[CH:11][CH:12]=2)[CH:6]=1)=[O:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 86711613HCID 86711613, compound

Product 1

HCID 86711612HCID 86711612, compound

Conditions

Temperature
70 °C

Procedure

To a solution of preparation 4a (1.8 g, 90% purity, 6.95 mmol) in methanol (5 mL) is added slowly thionyl chloride (1.64 g, 13.8 mmol) at 0° C. The reaction mixture is stirred at 70° C. for 1.5 h, concentrated under reduced pressure and purified by reversed-phase HPLC (Gilson: Sunfire, 30° C., gradient of acetonitrile in water+0.1% formic acid). Yield: 199 mg (12% of theory). ESI mass spectrum: [M+H]+=248; r.t. HPLC: 0.56 min (Z018_S04).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by reversed-phase HPLC (Gilson: Sunfire, 30° C., gradient of acetonitrile in water+0.1% formic acid)
  3. customr.t
  4. custom0.56 min (Z018_S04)

Sources & evidence

ORD record
ord-7cf0e3abd5064bf2a84e3b80bffea3a0
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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