Methanol → HCID 73043127, compound

HRID 2380756Notes

Reaction equation

HRID 2380756 reaction equation
[C:1]1([CH2:7][C:8](=[N:12][NH:13][C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:18]=2)[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH3:29]O>>[CH3:29][O:10][C:9](=[O:11])[C:8](=[N:12][NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:18]=1)[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 73021162HCID 73021162, compound

Product 1

HCID 73043127HCID 73043127, compound

Procedure

To a suspension of 4b (0.1 mmol, 34 mg) in MeOH (2 mL), was added dropwise thionylchloride (22 μL, 0.3 mmol) at −30° C. Then, the solution was allowed to warm at room temperature. The reaction mixture was heated to reflux and concentrated to afford the desired product. The crude is purified by silica gel chromatography (EtOAc/MeOH 10/1) to give the pure compound as a yellow solid (11 mg, 32%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6d165cf6385346118b6f3a14643d5775
Source dataset
uspto-grants-2012_09
Patent number
US08257931B2

Reaction notes

Loading…