Isobutyryl chloride → N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylcarbamothioyl)isobutyramide

HRID 2061163Notes

Reaction equation

[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[N-:7]=[C:8]=[S:9].[NH4+].[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:31])=[C:16]([C:18]2[C:19](=[O:30])[N:20]([CH3:29])[C:21]3[C:26]([CH:27]=2)=[CH:25][N:24]=[C:23]([CH3:28])[CH:22]=3)[CH:17]=1>CC(C)=O>[CH3:29][N:20]1[C:21]2[C:26](=[CH:25][N:24]=[C:23]([CH3:28])[CH:22]=2)[CH:27]=[C:18]([C:16]2[CH:17]=[C:12]([NH:11][C:8]([NH:7][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])=[S:9])[CH:13]=[CH:14][C:15]=2[CH3:31])[C:19]1=[O:30]

Participants

Conditions

Temperature: 40 °C

Procedure

The mixture of isobutyryl chloride (160 mg, 1.5 mmol) and ammonium isothiocyanate (114.2 mg, 1.5 mmol) in acetone (2.0 mL) was heated at 40° C. for 3 h. To the above reaction mixture, 3-(5-amino-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one (15) (419 mg, 1.5 mmol) was added at rt and stirred for 30 min. The solvent was removed under vacuum to yield N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylcarbamothioyl)isobutyramide 22, which was used without purification. MS m/z 409.2 (M+1).

Workup

customThe solvent was removed under vacuum

Sources & evidence

ORD record: ord-d132d574c162467db04ad2b18c3fb26e
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278452B2

Reaction notes

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