Reaktion #165458

Reaktionsgleichung

3-(3-(6-benzyloxy-pyridin-3-ylmethyl)-isoxazol-5-yl)-pyridin-2,6-diamine

glyoxylic acid ethyl ester

α-picoline borane

sodium hydrogencarbonate

→

title compound

Ausbeute 8.0%

(6-Amino-5-(3-(6-benzyloxy-pyridin-3-ylmethyl)-isoxazol-5-yl)-pyridin-2-ylamino)-acetic acid ethyl ester

Ausbeute 8.0%

Lösungsmittel

N,N-dimethylformamide

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionwas extracted with ethyl acetate
2. 2
   WaschenThe organic layer was washed with saturated aqueous sodium chloride
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Einengenafter which the organic layer was concentrated under a reduced pressure
5. 5
   SonstigeThe residue thus obtained
6. 6
   Sonstigewas purified by reverse-phase high performance liquid chromatography (
7. 7
   workup.ADDITIONcontaining 0.1% trifluoroacetic acid)

Vorschrift

To a mixture of 3-(3-(6-benzyloxy-pyridin-3-ylmethyl)-isoxazol-5-yl)-pyridin-2,6-diamine (40 mg, 0.11 mmol) described in Example 25 and N,N-dimethylformamide (0.5 mL) were added glyoxylic acid ethyl ester polymer foam (16 mg, 0.16 mmol), α-picoline-borane (14 mg, 0.13 mmol), and acetic acid (40 mL), which was stirred overnight at the same temperature. A saturated sodium hydrogencarbonate aqueous solution was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, after which the organic layer was concentrated under a reduced pressure. The residue thus obtained was purified by reverse-phase high performance liquid chromatography (using an acetonitrile-water mobile phase containing 0.1% trifluoroacetic acid) to obtain the title compound (4.9 mg, 8%) as a trifluoroacetic acid salt.

Quelle