Sodium Bicarbonate → N-[2-(S)-(3,4-dichlorophenyl)-4-hydroxybutyl]-N-methyl-3cyano-2methoxy-1-naphthamide

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Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:13][CH2:14][OH:15])[CH2:10][NH:11][CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)(O)[O-].[Na+].[C:21]([C:23]1[C:24]([O:36][CH3:37])=[C:25]([C:33](Cl)=[O:34])[C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2)#[N:22]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:13][CH2:14][OH:15])[CH2:10][N:11]([CH3:12])[C:33]([C:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:32]=[C:23]([C:21]#[N:22])[C:24]=2[O:36][CH3:37])=[O:34])[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of N-[2-(S)-(3,4-dichlorophenyl)-4-hydroxybutyl]-N-methylamine (Miller, SC; WO 9512577) in DCM was combined with 10% aqueous sodium bicarbonate solution. The mixture was cooled to 0° C. and a solution of 3-cyano-2-methoxy-1-naphthoyl chloride (prepared from 3-cyano-2-methoxy-1-naphthoic acid using oxalyl chloride) in DCM was added dropwise over 30 min. After stirring overnight at room temperature, the organic phase was concentrated and purified by column chromatography to afford N-[2-(S)-(3,4-dichloro-phenyl)-4-hydroxybutyl]-N-methyl-3-cyano-2-methoxy-1-naphathamide. 1H NMR (300 MHz, DMSO-d6) δ 8.67-8.58 (m), 8.07-8.00 (m), 7.72-7.65 (m), 7.64-7.43 (m), 7.42-7.34 (m), 7.02-7.01 (m), 6.98-6.87 (d), 6.77-6.74 (d), 6.31-6.28 (d), 4.55-4.52 (t), 4.35-4.34 (t), 4.03-3.92 (m), 3.78-3.72 (m), 3.68 (s), 3.45-3.37 (m), 3.29-2.89 (m), 2.73 (s), 2.59-2.49 (m), 1.91-1.78 (m), 1.58-1.46 (m); MS APCI, m/z=457 (M+). (g) N-[2-(S)-(3,4-Dichlorophenyl)-3-carboxypropyl]—N-methyl-3-cyano-2-methoxy-1-naphthamide

Aufarbeitung

concentrationthe organic phase was concentrated
custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-d432850154ef4961a1573b1c991704a0
Quelldatensatz: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06903092B2

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