(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 931629Notes

Reaction equation

HRID 931629 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

(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].

Workup

  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)

Sources & evidence

ORD record
ord-d407eea17ddc451999fb2c0ec1a7a9c4
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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