4-(5-Amino-6-(phenylmethyl)-2-pyrazinyl)phenol → 2-((3-Benzyl-5-(4-hydroxyphenyl)pyrazin-2-yl)amino)hexanoic acid

HRID 2407198

Reaktionsgleichung

[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[N:6][C:7]=1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Na+].O=[C:24]([CH2:28][CH2:29][CH2:30][CH3:31])[C:25]([O-:27])=[O:26]>C(O)C.C(O)(=O)C.[Pd]>[CH2:8]([C:7]1[C:2]([NH:1][CH:24]([CH2:28][CH2:29][CH2:30][CH3:31])[C:25]([OH:27])=[O:26])=[N:3][CH:4]=[C:5]([C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)[N:6]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

4-(5-amino-6-benzylpyrazin-2-yl)phenol (200 mg, 0.72 mmol) was mixed with 2-Ketohexanoic acid sodium salt (220 mg, 1.44 mmol) in ethanol (20 mL). Pd/C (10% Palladium in active carbon, 100 mg) was added with a few drops of acetic acid, and the reaction mixture heated to 65° C. Air was bubbled out by N2 gas, and a hydrogen balloon applied to the reaction flask. The reaction was continuously stirred for 4 hrs. After cooling down, it was filtered and the resulting solution was purified by flash chromatography (eluting solvent: 50% EtOAc in heptanes) to give the product as a yellow powder (130 mg, 46%). MS (ESI): m/z 392.2 (M+1).

Aufarbeitung

customAir was bubbled out by N2 gas
temperatureAfter cooling down
filtrationit was filtered
customthe resulting solution was purified by flash chromatography (eluting solvent: 50% EtOAc in heptanes)

Quellen und Nachweise

ORD-Eintrag: ord-47f86147d4124894872c2d05d8736a0c
Quelldatensatz: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08809529B2

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