(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 931629노트

반응식

HRID 931629 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

HCID 89473235(S)-N7'-(3-ethoxypyridin-2-yl)-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthene]-2,7'-diamine수율 25.1%

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 887Methanol용매

실험 절차

(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].

후처리

  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)

출처 및 근거

ORD 기록
ord-d407eea17ddc451999fb2c0ec1a7a9c4
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296759B2

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