(S)-N-(7-((3-ethoxypyridin-2-yl)amino)-4-fluoro-9-(2-hydroxyethyl)-2-methoxy-9H-xanthen-9-yl)cyanamide → (S)-N7'-(3-ethoxypyridin-2-yl)-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthene]-2,7'-diamine

HRID 931629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931629
[CH2:1]([O:3][C:4]1[C:5]([NH:10][C:11]2[CH:24]=[C:23]3[C:14]([O:15][C:16]4[C:17]([F:33])=[CH:18][C:19]([O:31][CH3:32])=[CH:20][C:21]=4[C@:22]3([NH:28][C:29]#[N:30])[CH2:25][CH2:26][OH:27])=[CH:13][CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]>CO.Cl>[CH2:1]([O:3][C:4]1[C:5]([NH:10][C:11]2[CH:24]=[C:23]3[C:14]([O:15][C:16]4[C:17]([F:33])=[CH:18][C:19]([O:31][CH3:32])=[CH:20][C:21]=4[C@@:22]43[CH2:25][CH2:26][O:27][C:29]([NH2:30])=[N:28]4)=[CH:13][CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

Komponenten

4

Edukt 1

HCID 89461784(S)-N-(7-((3-ethoxypyridin-2-yl)amino)-4-fluoro-9-(2-hydroxyethyl)-2-methoxy-9H-xanthen-9-yl)cyanamide

Produkt 1

HCID 89473235(S)-N7'-(3-ethoxypyridin-2-yl)-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthene]-2,7'-diamineAusbeute 25,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

(S)—N-(7-((3-ethoxypyridin-2-yl)amino)-4-fluoro-9-(2-hydroxyethyl)-2-methoxy-9H-xanthen-9-yl)cyanamide (160 mg, 0.355 mmol) was dissolved in methanol (10 ml) and three drops of concentrated HCl was added. The solution was stirred at room temperature for 30 minutes. The solution was quenched with water and saturated sodium bicarbonate, then extracted with ethyl acetate. The organics were then separated and concentrated. The product was purified via silica gel column chromatography (RediSep 40 g column) using 50-100% ethyl acetate in heptane to afford (S)—N7′-(3-ethoxypyridin-2-yl)-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthene]-2,7′-diamine (40 mg, 0.089 mmol, 25.00% yield). MS m/z=451.0 [M+H].

Aufarbeitung

  1. customThe solution was quenched with water and saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. customThe organics were then separated
  4. concentrationconcentrated
  5. customThe product was purified via silica gel column chromatography (RediSep 40 g column)

Quellen und Nachweise

ORD-Eintrag
ord-d407eea17ddc451999fb2c0ec1a7a9c4
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296759B2

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