5-Iodosalicylic acid → (s)-2-Hydroxy-5-{[5-({[methyl(oxo)phenyl-lambda6-sulfanylidene]amino}carbonyl)pyridin-3-yl]ethynyl}benzoic acid

HRID 391526Notes

Reaction equation

HRID 391526 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH:20]=1)[C:8]([N:10]=[S@@:11]([CH3:19])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])#[CH:2].I[C:22]1[CH:30]=[C:26]([C:27]([OH:29])=[O:28])[C:25]([OH:31])=[CH:24][CH:23]=1>>[OH:31][C:25]1[CH:24]=[CH:23][C:22]([C:2]#[C:1][C:3]2[CH:4]=[N:5][CH:6]=[C:7]([C:8]([N:10]=[S@@:11]([CH3:19])(=[O:18])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:9])[CH:20]=2)=[CH:30][C:26]=1[C:27]([OH:29])=[O:28]

Participants

3

Reactant 2

HCID 83885-Iodosalicylic acidHCID 24953136(S)-5-ethynyl-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide

Product 1

HCID 24953844(s)-2-Hydroxy-5-{[5-({[methyl(oxo)phenyl-lambda6-sulfanylidene]amino}carbonyl)pyridin-3-yl]ethynyl}benzoic acidYield 45%

Procedure

In a manner similar to that describe in Example 434, a mixture of (S)-5-ethynyl-N-[methyl(oxo)phenyl-λ6-sulfanylidene]nicotinamide and 5-iodosalicyclic acid were reacted to give the title compound as a light tan solid (28 mg, 45%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2ba09586f3944ac9adee28f74bc6abc9
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

Loading…