1-Cyclopropyl-3,3-bis(methylthio)prop-2-en-1-one → (Z)-3-(5-(3-cyclopropyl-1-(methylthio)-3-oxoprop-1-enylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one

HRID 2061192Notes

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.[CH:22]1([C:25](=[O:32])[CH:26]=[C:27](SC)[S:28][CH3:29])[CH2:24][CH2:23]1>O1CCOCC1>[CH:22]1([C:25](=[O:32])/[CH:26]=[C:27](/[NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]3[C:9](=[O:20])[N:10]([CH3:19])[C:11]4[C:16]([CH:17]=3)=[CH:15][N:14]=[C:13]([CH3:18])[CH:12]=4)[CH:7]=2)\[S:28][CH3:29])[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 150 °C

Procedure

The mixture of 3-(5-amino-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one 15 (165 mg, 0.589 mmol) and 1-cyclopropyl-3,3-bis(methylthio)prop-2-en-1-one 30 (111 mg, 0.589 mmol) in 1,4-dioxane (2 mL) was heated in a sealed vial at 150° C. overnight. The solvent was removed to yield crude (Z)-3-(5-(3-cyclopropyl-1-(methylthio)-3-oxoprop-1-enylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one 31 which was used without further purification. MS m/z 420.1 (M+1).

Workup

customThe solvent was removed

Sources & evidence

ORD record: ord-e2ee6330bfc34d81b2e1ce0e6b7805cd
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278452B2

Reaction notes

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