Sodium methanesulfinate → HCID 22508876, compound

HRID 1163054Notes

Reaction equation

HRID 1163054 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:26])[C:19]([O:21][CH2:22][CH:23]4[CH2:25][O:24]4)=[CH:20][N:16]3[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:27])[NH:6]2.[CH3:28][S:29]([O-:31])=[O:30].[Na+]>CS(C)=O>[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:26])[C:19]([O:21][CH2:22][CH:23]([OH:24])[CH2:25][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:20][N:16]3[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:27])[NH:6]2

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 22508879HCID 22508879, compound

Product 1

HCID 22508876HCID 22508876, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of Example 2 (10 mg, 0.027 mmol) and sodium methanesulfinate (120 mg, 85%, 1.0 mmol) in DMSO was heated at 105° C. for 1 hr. The mixture was concentrated and purified by chromatography on silica gel eluting with 5% methanol in ethyl acetate to provide the title compound (5.5 mg, 45%) as a white solid. MS: (M+H)+=449.3

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by chromatography on silica gel eluting with 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-bd004b0aa5e741fdb761629fc97340fd
Source dataset
uspto-grants-2010_10
Patent number
US07820814B2

Reaction notes

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