N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine → N-[(6-chloropyridin-3-yl)methyl]-N-(2,2-difluoroethyl)-4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxamide

HRID 1192839

Reaction equation

[OH:1][C:2]1[CH2:6][O:5][C:4](=[O:7])[C:3]=1[C:8]([O:10]C)=O.[Cl:12][C:13]1[N:18]=[CH:17][C:16]([CH2:19][NH:20][CH2:21][CH:22]([F:24])[F:23])=[CH:15][CH:14]=1>C(#N)CCC>[Cl:12][C:13]1[N:18]=[CH:17][C:16]([CH2:19][N:20]([CH2:21][CH:22]([F:24])[F:23])[C:8]([C:3]2[C:4](=[O:7])[O:5][CH2:6][C:2]=2[OH:1])=[O:10])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 65 °C

Procedure

10 g of methyl 4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxylate are initially introduced in 111 g of butyronitrile and admixed with 5 g of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine. The solution is heated at 65° C. for 3 h. The solution is then extracted with 300 ml of water and then washed with 300 ml of 5% strength hydrochloric acid solution. The organic phase is dried over magnesium sulphate and the solvent is removed in vacuo. For purification, recrystallization from isopropanol is carried out.

Workup

extractionThe solution is then extracted with 300 ml of water
washwashed with 300 ml of 5% strength hydrochloric acid solution
dry with materialThe organic phase is dried over magnesium sulphate
customthe solvent is removed in vacuo
customFor purification, recrystallization from isopropanol

Sources & evidence

ORD record: ord-33b2f7e565e44cbd870ad14183a7eeae
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680285B2

Linked notes

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