5-((3-(3-Methylfuran-2-carboxamido)phenyl)ethynyl)nicotinic acid → N-{[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl](methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamide

HRID 607426Notes

Reaction equation

HRID 607426 reaction equation
[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[NH:16])=[O:15])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][C:21]1[CH:25]=[CH:24][O:23][C:22]=1[C:26]([NH:28][C:29]1[CH:30]=[C:31]([C:35]#[C:36][C:37]2[CH:38]=[N:39][CH:40]=[C:41]([CH:45]=2)[C:42](O)=[O:43])[CH:32]=[CH:33][CH:34]=1)=[O:27]>>[Si:5]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH3:17])(=[O:15])=[N:16][C:42](=[O:43])[C:41]2[CH:45]=[C:37]([C:36]#[C:35][C:31]3[CH:32]=[CH:33][CH:34]=[C:29]([NH:28][C:26]([C:22]4[O:23][CH:24]=[CH:25][C:21]=4[CH3:20])=[O:27])[CH:30]=3)[CH:38]=[N:39][CH:40]=2)=[CH:12][CH:13]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 576578475-((3-(3-Methylfuran-2-carboxamido)phenyl)ethynyl)nicotinic acidHCID 57657970tert-Butyl(dimethyl) {[4-(S-methylsulfonimidoyl)benzyl]oxy}silane

Product 1

HCID 57657965N-{[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl](methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamideYield 71%

Procedure

In a manner similar to that described in Example 480 (step 6), tert-Butyl(dimethyl) {[4-(S-methylsulfonimidoyl)benzyl]oxy}silane (0.485 g, 1.62 mmol) and 5-((3-(3-methylfuran-2-carboxamido)phenyl)ethynyl)nicotinic acid (0.561 g, 1.62 mmol) were reacted to give the title compound (0.722 g, 71%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-8d1014934ece46a387e590707d91383f
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Reaction notes

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