2-benzoyl-N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)hydrazinecarbothioamide → 1,7-dimethyl-3-(2-methyl-5-(5-phenyl-1,3,4-thiadiazol-2-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one

HRID 2061197Notes

Reaction equation

[C:1]([NH:9][NH:10][C:11](=[S:33])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([C:20]2[C:21](=[O:32])[N:22]([CH3:31])[C:23]3[C:28]([CH:29]=2)=[CH:27][N:26]=[C:25]([CH3:30])[CH:24]=3)[CH:14]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CS(O)(=O)=O.C1(C)C=CC=CC=1>[CH3:31][N:22]1[C:23]2[C:28](=[CH:27][N:26]=[C:25]([CH3:30])[CH:24]=2)[CH:29]=[C:20]([C:15]2[CH:14]=[C:13]([NH:12][C:11]3[S:33][C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[N:9][N:10]=3)[CH:18]=[CH:17][C:16]=2[CH3:19])[C:21]1=[O:32]

Participants

Conditions

Temperature: 130 °C

Procedure

The mixture of crude 2-benzoyl-N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)hydrazinecarbothioamide 35 and methanesulfonic acid (2 drops) in toluene (1 mL) was heated at 130° C. overnight in a sealed vial. The reaction was evaporated to dryness and the crude residue was purified by preparative LC/MS to give 1,7-dimethyl-3-(2-methyl-5-(5-phenyl-1,3,4-thiadiazol-2-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one (H1). MS m/z 440.1 (M+1).

Workup

customThe reaction was evaporated to dryness
customthe crude residue was purified by preparative LC/MS

Sources & evidence

ORD record: ord-27f6ad71a6024ff3ad2ed333a05ed81d
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278452B2

Reaction notes

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