Water → HCID 57411324, compound

HRID 1502334Notes

Reaction equation

HRID 1502334 reaction equation
[CH:1]([S:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:11]=[CH:12]2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[OH:21]OS([O-])=O.[K+].[OH2:27]>CO>[CH:1]([S:4]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:11]=[CH:12]2)=[CH:7][CH:6]=1)=[O:21])([CH3:3])[CH3:2].[CH:1]([S:4]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:11]=[CH:12]2)=[CH:7][CH:6]=1)(=[O:21])=[O:27])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 57411213HCID 57411213, compound

Product 2

HCID 57411323HCID 57411323, compoundYield 24.7%HCID 57411324HCID 57411324, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(7-(isopropylthio)isoquinolin-3-yl)cyclopropanecarboxamide (see, Example 80) (85.8 mg, 0.35 mmol) in methanol (15 mL) was added a solution of Oxone (1 eq) in water (15 mL) at 0° C. It was warmed to room temperature and stirred for 5 hours. The reaction mixture was concentrated under reduced pressure and purified by prep-TLC to give the products N-(7-(isopropylsulfinyl)isoquinolin-3-yl)cyclopropanecarboxamide (26.1 mg, 24.7%) and N-(7-(isopropylsulfonyl)isoquinolin-3-yl)cyclopropanecarboxamide (28.1 mg, 25.2%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by prep-TLC

Sources & evidence

ORD record
ord-c2a0346a4b804d9f896f259c09657776
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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