Dimethyl Sulfate → N-[6-amino-2-(2-phenylethynyl)pyridin-3-yl]-N-methylbenzenesulfonamide

HRID 535403Notes

Reaction equation

HRID 535403 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:6][CH:5]=1.[CH3:28]OS(OC)(=O)=O>C1COCC1>[NH2:3][C:4]1[N:9]=[C:8]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([N:18]([CH3:28])[S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 86694380N-[6-amino-2-(2-phenylethynyl)pyridin-3-yl]benzenesulfonamide

Product 1

HCID 86694389N-[6-amino-2-(2-phenylethynyl)pyridin-3-yl]-N-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At RT NaH (60% dispersion in mineral oil, 4.6 mg, 0.12 mmol) is added to N-[6-amino-2-(2-phenylethynyl)pyridin-3-yl]benzenesulfonamide D5a (27 mg, approx. 0.07 mmol) in THF (0.6 ml). After stirring for 10 minutes dimethylsulfate (8 μl, 0.08 mmol) is added to the mixture and stirring continued for 1 h. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 16 mg (57%). HPLC-MS: M+H=364; tR=1.85 min (*Method—2).

Workup

  1. additionis added to the mixture
  2. concentrationThe mixture is concentrated in vacuo
  3. customthe product purified by RP HPLC

Sources & evidence

ORD record
ord-6d4dcf2a5f9144a2ab6b642d8ebd011f
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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