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

HRID 2061163
Notes
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Reaction equation

HRID 2061163 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 592123103-(5-amino-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-oneHCID 178514171HCID 178514171, compound

Product 1

HCID 58369052N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylcarbamothioyl)isobutyramide

Reagents, catalysts & solvents 1

HCID 180Acetone
Solvent

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

  1. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes