(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 931629ノート

反応式

HRID 931629 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 887Methanol溶媒

実験手順

(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].

後処理

  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)

出典と根拠

ORDレコード
ord-d407eea17ddc451999fb2c0ec1a7a9c4
出典データセット
uspto-grants-2016_03
特許番号
US09296759B2

反応ノート

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