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

HRID 2061188Notes

Reaction equation

[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N-:9]=[C:10]=[S:11].[NH4+].[NH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:33])=[C:18]([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:19]=1>CC(C)=O>[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:18]2[CH:19]=[C:14]([NH:13][C:10]([NH:9][C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])=[S:11])[CH:15]=[CH:16][C:17]=2[CH3:33])[C:21]1=[O:32]

Participants

Conditions

Temperature: 40 °C

Procedure

The mixture of cyclopentanecarbonyl chloride (13 mg, 0.1 mmol) and ammonium isothiocyanate (7.6 mg, 0.1 mmol) in acetone (1.0 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) (27.5 mg, 0.1 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)cyclopentanecarboxamide 27, which was used without purification. MS m/z 435.2 (M+1).

Workup

customThe solvent was removed under vacuum

Sources & evidence

ORD record: ord-524181c6751b4f5da148e98abd5c6aa4
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278452B2

Reaction notes

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