6059-44-5 → HCID 58094889, compound

HRID 2402480Notes

Reaction equation

[Br:1][C:2]1[S:6][C:5]([C:7](=[NH:11])OCC)=[C:4]([C:12]2(Cl)[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH2:13]2)[C:3]=1[C:20]#[N:21].[ClH:22].Cl.N[CH:25]([CH2:30][NH2:31])[C:26]([O:28][CH3:29])=[O:27]>C(O)C>[Br:1][C:2]1[S:6][C:5]([C:7]2[NH:11][CH:25]([C:26]([O:28][CH3:29])=[O:27])[CH2:30][N:31]=2)=[C:4]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][C:17]=2[Cl:22])[C:3]=1[C:20]#[N:21]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 5-bromo-4-cyano-3-(1,4-dichlorophenyl)thiophene-2-carboximidoate (0.548 g, 1.36 mmol) in ethanol (26 mL) was added methyl 2,3-diaminopropanoate dihydrochloride (0.313 g, 1.64 mmol). The solution was stirred at 80° C. for 4 hours. The solvent was evaporated, and column chromatography was performed to yield the title compound (0.222 g, 36%). LCMS: (FA) ES+ 460. 1H NMR (400 MHz, d4-methanol) 7.70 (s, 1H), 7.55-7.43 (m, 2H), 3.76-3.66 (m, 4H), 1.36-1.26 (m, 3H).

Workup

customThe solvent was evaporated

Sources & evidence

ORD record: ord-fad982dbd1ff487c9d72879607ed3cc4
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796314B2

Reaction notes

Loading…