Thiophenol → HCID 178516460, compound

HRID 1028048Notes

Reaction equation

HRID 1028048 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[CH:6][C:5]=1[NH:11]S(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O)(=[O:3])[CH3:2].[CH3:24]CN(C(C)C)C(C)C.C1(S)C=CC=CC=1>CN(C=O)C>[Cl:10][C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][N:7]=1)[N:11]=[CH:24][CH:2]=[C:1]2[OH:3]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 81531DiisopropylethylamineHCID 86656449HCID 86656449, compound

Product 1

HCID 178516460HCID 178516460, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-acetyl-6-chloropyridin-3-yl)-4-nitrobenzenesulfonamide (1.0 equiv.), dimethylformamidedimethylacetal (4.8 equiv.) and DIEA (4.8 equiv.) in DMF (0.15 M) was heated under Ar at 110° C. for 96 hours. Upon cooling, thiophenol (4.9 equiv.) was added and the solution was stirred at rt for 15 hours. The volatiles were removed in vacuo and following silica gel purification (0-1.5-3-5% MeOH/CH2Cl2) 6-chloro-1,7-naphthyridin-4-ol was obtained (55%). LC/MS=180.9/182.9 (M+H), LC=1.41 min

Workup

  1. temperatureUpon cooling
  2. customThe volatiles were removed in vacuo
  3. customsilica gel purification (0-1.5-3-5% MeOH/CH2Cl2) 6-chloro-1,7-naphthyridin-4-ol
  4. customwas obtained (55%)
  5. customLC/MS=180.9/182.9 (M+H), LC=1.41 min

Sources & evidence

ORD record
ord-c3eff5f6ecd34be8abab465be3ad6553
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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