HCID 9813537, compound → HCID 22477492, compound

HRID 1835198Notes

Reaction equation

HRID 1835198 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:17][C:12]3=[N:13][CH:14]=[CH:15][N:16]=[C:11]3[CH:10]=2)=[CH:5][CH:4]=1.[OH:18]OS([O-])=O.[K+]>ClCCl>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[NH:17][C:12]3=[N:13][CH:14]=[CH:15][N:16]=[C:11]3[CH:10]=2)=[CH:7][CH:8]=1)=[O:18]

Participants

4

Reactant 2

HCID 9813537HCID 9813537, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22477492HCID 22477492, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 6-(4-methylthiophenyl)-5H-pyrrolo[2,3-b]pyrazine [0.2362 g, Example 1(ah)] in dichloromethane (20 mL) was treated with TBA oxone (2.545 g). After 2 hours the resulting orange solution was evaporated. The residue was subjected to flash chromatography eluting with a mixture of methanol and dichloromethane (1:1, v/v) to give the title compound as a white solid. MS: 258 (MH+). 1H NMR [(CD3)2SO]: δ 12.66 (1H, s); 8.41 (1H, s); 8.24 (3H, m); 7.82 (2H, d, J=8.7 Hz); 7.33 (1H, s); 2.81 (3H, s).

Workup

  1. customAfter 2 hours the resulting orange solution was evaporated
  2. washeluting with a mixture of methanol and dichloromethane (1:1

Sources & evidence

ORD record
ord-f5f05041138c46f5a3184d4633b0e20a
Source dataset
uspto-grants-2004_08
Patent number
US06770643B2

Reaction notes

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