Methylamine → 5-[(3-hydroxyphenyl)ethynyl]-N-{[2-(methylamino)-2-oxoethyl](oxo)phenyl-lambda6-sulfanylidene}nicotinamide

HRID 391573Notes

Reaction equation

HRID 391573 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[C:12]([C:16]([N:18]=[S@:19]([CH2:27][C:28]([O:30]CC)=O)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:20])=[O:17])[CH:13]=[N:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:33][NH2:34]>>[OH:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:15]=[N:14][CH:13]=[C:12]([CH:11]=2)[C:16]([N:18]=[S:19]([CH2:27][C:28]([NH:34][CH3:33])=[O:30])(=[O:20])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:17])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 24954917(S)-Ethyl [N-({5-[(3-hydroxyphenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]acetate

Product 1

HCID 576578245-[(3-hydroxyphenyl)ethynyl]-N-{[2-(methylamino)-2-oxoethyl](oxo)phenyl-lambda6-sulfanylidene}nicotinamideYield 90.2%

Procedure

In a manner similar to that described for Example 471, (S)-Ethyl [N-({5-[(3-hydroxyphenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]acetate (50 mg, 0.11 mmol) and methylamine (2.0 M solution in MeOH, 0.5 mL, 1.0 mmol) were reacted to give the title compound as colorless oil (43 mg, 90%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ec5d92b35d8a4c4da01e34e8bd8edb8b
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

Loading…