p-Chlorothiophenol → (S)-2-{[1-(4-Chloro-phenylsulfanyl)-4-hydroxy-isoquinoline-3-carbonyl]-amino}-propionic acid

HRID 250345Notes

Reaction equation

HRID 250345 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([NH:15][C@@H:16]([CH3:20])[C:17]([OH:19])=[O:18])=[O:14])[N:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1>>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([OH:12])=[C:4]([C:13]([NH:15][C@@H:16]([CH3:20])[C:17]([OH:19])=[O:18])=[O:14])[N:3]=2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 7815p-ChlorothiophenolHCID 86595466(S)-2-{[1-bromo-4-hydroxy-isoquinoline-3-carbonyl]-amino}-propionic acid

Product 1

HCID 66713177(S)-2-{[1-(4-Chloro-phenylsulfanyl)-4-hydroxy-isoquinoline-3-carbonyl]-amino}-propionic acidYield 6.1%

Conditions

Temperature
210 °C

Procedure

To a solution of 250 mg of (S)-2-{[1-bromo-4-hydroxy-isoquinoline-3-carbonyl]-amino}-propionic acid in 0.7 ml of 1-methyl-2-pryrrolidinone was added 433 mg of 4-chloro-benzenethiol. The solution was heated at 210° C. for 30 min. using a CEM Discover microwave reactor. The solution was concentrated under vacuum. The resultant residue was crystallized from methanol to yield 18 mg of a tan solid; MS (−): m/z 401.10 (M−1)

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. customThe resultant residue was crystallized from methanol

Sources & evidence

ORD record
ord-663784324563488a8ede8b126f868cf6
Source dataset
uspto-grants-2011_01
Patent number
US07863292B2

Reaction notes

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