Sodium Hydroxide → 4-{benzyl[(6-chloropyridin-3-yl)methyl]amino}furan-2(5H)-one

HRID 451339Notes

Reaction equation

[CH2:1]([NH:8][C:9]1[CH2:13][O:12][C:11](=[O:14])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][N:19]=1>C(COC)OC>[CH2:1]([N:8]([CH2:24][C:21]1[CH:20]=[N:19][C:18]([Cl:17])=[CH:23][CH:22]=1)[C:9]1[CH2:13][O:12][C:11](=[O:14])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

6.3 g of 4-(benzylamino)furan-2(5H)-one (Example 16) are initially charged in 75 ml of dimethoxyethane at room temperature. Subsequently, 1.1 g of sodium hydroxide are added and, at 40° C. 25.5 g of a 20% solution of 2-chloro-5-(chloromethyl)pyridine in dimethoxyethane are metered in. The mixture is stirred at 50° C. for a further 6 h. The solvent is substantially removed under reduced pressure and the residue is admixed with 50 ml of water and 50 ml of methylene chloride. The organic phase is removed, and the aqueous phase is extracted once again with 50 ml of methylene chloride. The combined methylene chloride phases are dried over sodium sulphate and the solvent is removed under reduced pressure. 8 g of 4-{benzyl[(6-chloropyridin-3-yl)methyl]amino}furan-2(5H)-one are obtained (this corresponds to 85% yield).

Workup

customThe solvent is substantially removed under reduced pressure
customThe organic phase is removed
extractionthe aqueous phase is extracted once again with 50 ml of methylene chloride
dry with materialThe combined methylene chloride phases are dried over sodium sulphate
customthe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-147620f2416f4eff977911e42f513fda
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487112B2

Reaction notes

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