Pyridine → N-{2-Methoxy-5-[2-(3-propyl-[1,2,4]oxadiazol-5-yl)-vinyl]-phenyl}-methane sulfonamide

HRID 470613Notes

Reaction equation

HRID 470613 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[O:15][N:14]=[C:13]([CH2:16][CH2:17][CH3:18])[N:12]=2)=[CH:5][C:4]=1[NH2:19].N1C=CC=CC=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[O:15][N:14]=[C:13]([CH2:16][CH2:17][CH3:18])[N:12]=2)=[CH:5][C:4]=1[NH:19][S:27]([CH3:26])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 673983662-Methoxy-5-[2-(3-propyl-[1,2,4]oxadiazol-5-yl)-vinyl]-phenylamine2×

Product 1

HCID 67396842N-{2-Methoxy-5-[2-(3-propyl-[1,2,4]oxadiazol-5-yl)-vinyl]-phenyl}-methane sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxy-5-[2-(3-propyl-[1,2,4]oxadiazol-5-yl)-vinyl]-phenylamine (compound of Example 8; 0.08 g, 3.08 mmol) was dissolved in dichloromethane (10 mL) followed by addition of pyridine (0.047 mL, 0.60 mmol) and methanesulfonyl chloride (0.034 mL, 0.45 mmol) at room temperature. After stirring for 8 h, dichloromethane was evaporated and the reaction mixture was cooled to room temperature. The crude residue obtained was purified by column chromatography (silica gel, petroleum ether) to afford the title compound.

Workup

  1. customdichloromethane was evaporated
  2. customThe crude residue obtained
  3. customwas purified by column chromatography (silica gel, petroleum ether)

Sources & evidence

ORD record
ord-b35b09298ed847bdbaadf334d02ebc51
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Reaction notes

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