2-(Methylamino)ethanol → (S)-N-[{2-[(2-hydroxyethyl)(methyl)amino]-2-oxoethyl}(oxo)phenyl-lambda6-sulfanylidene]-5-[(3-hydroxyphenyl)ethynyl]nicotinamide

HRID 391572Notes

Reaction equation

HRID 391572 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](OCC)=[O:29])([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][NH:34][CH2:35][CH2:36][OH:37]>>[OH:37][CH2:36][CH2:35][N:34]([CH3:33])[C:28](=[O:29])[CH2:27][S@:19](=[O:20])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[N:18][C:16](=[O:17])[C:12]1[CH:11]=[C:10]([C:9]#[C:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=2)[CH:15]=[N:14][CH:13]=1

Participants

3

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 24954917(S)-Ethyl [N-({5-[(3-hydroxyphenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]acetate

Product 1

HCID 24954919(S)-N-[{2-[(2-hydroxyethyl)(methyl)amino]-2-oxoethyl}(oxo)phenyl-lambda6-sulfanylidene]-5-[(3-hydroxyphenyl)ethynyl]nicotinamideYield 62.8%

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 (65 mg, 0.14 mmol) and 2-(methylamino)ethanol (0.1 mL, 1.2 mmol) were reacted to give the title as clear oil (42 mg, 61%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ba1b497ec0f946f2a4ac3f95e60403a1
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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