Diisopropylethylamine → Methanesulfonamide, N-[2-[(2-cyano-3-pyridinyl)amino]ethyl]-N-methyl-

HRID 1179310Notes

Reaction equation

HRID 1179310 reaction equation
[Cl-].[CH3:2][N:3]([S:7]([CH3:10])(=[O:9])=[O:8])[CH2:4][CH2:5][NH3+:6].F[C:12]1[C:13]([C:18]#[N:19])=[N:14][CH:15]=[CH:16][CH:17]=1.CCN(C(C)C)C(C)C>CS(C)=O>[C:18]([C:13]1[C:12]([NH:6][CH2:5][CH2:4][N:3]([CH3:2])[S:7]([CH3:10])(=[O:9])=[O:8])=[CH:17][CH:16]=[CH:15][N:14]=1)#[N:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 70604082-Cyano-3-fluoropyridineHCID 87801618HCID 87801618, compound

Product 1

HCID 58977993Methanesulfonamide, N-[2-[(2-cyano-3-pyridinyl)amino]ethyl]-N-methyl-

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a manner similar to that described for Example 2, 2-[methyl(methylsulfonyl)amino]ethanaminium chloride (4 g, 25.4 mmol) was dissolved in DMSO (20 mL) and treated with 3-fluoro-2-cyanopyridine (2.5 g, 21.2 mmol) and Hunig's base (4.4 mL, 25.4 mmol) and heated to 90 degrees under pressure. The product was isolated as an oily off-white solid.

Workup

  1. temperatureheated to 90 degrees under pressure
  2. customThe product was isolated as an oily off-white solid

Sources & evidence

ORD record
ord-496c38a8eb7642d690a3c0936ec17563
Source dataset
uspto-grants-2007_10
Patent number
US07279487B2

Reaction notes

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