p-Toluenesulfonic acid → HCID 44201106, compound

HRID 2061195Notes

Reaction equation

HRID 2061195 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[C:9](=[O:20])[N:10]([CH3:19])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([CH3:18])[CH:12]=3)[CH:7]=1.Cl[C:23]1[N:27]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[S:25][N:24]=1.CC1C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[CH3:19][N:10]1[C:11]2[C:16](=[CH:15][N:14]=[C:13]([CH3:18])[CH:12]=2)[CH:17]=[C:8]([C:6]2[CH:7]=[C:2]([NH:1][C:23]3[N:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[S:25][N:24]=3)[CH:3]=[CH:4][C:5]=2[CH3:21])[C:9]1=[O:20]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 42473943-chloro-5-phenyl-1,2,4-thiadiazoleHCID 592123103-(5-amino-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one

Product 1

HCID 44201106HCID 44201106, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-(5-Amino-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one 15 (30 mg, 0.107 mmol), 3-chloro-5-phenyl-1,2,4-thiadiazole (41 mg, 0.21 mmol) and TsOH (10 mg) were heated at 100° C. in dioxane (2 ml). After 10 h, the solution was cooled and filtered. The mixture was purified by preparative LC/MS to give 1,7-dimethyl-3-(2-methyl-5-(5-phenyl-1,2,4-thiadiazol-3-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one (G1). MS m/z 440.5 (M+1).

Workup

  1. temperaturethe solution was cooled
  2. filtrationfiltered
  3. customThe mixture was purified by preparative LC/MS

Sources & evidence

ORD record
ord-69daf83566924d2cbb3a30b5b7184d42
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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