Réaction #57132

ord-306d460a146346a0aced3d03bf0681fa

Équation de réaction

O
water
CCn1cc(-c2ccnc3[nH]ccc23)c(-c2ccc(N)cc2)n1
4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]aniline
CCN(CC)CC
triethylamine
O=C(Cl)N1CCOCC1
4-morpholinecarbonyl chloride
CCn1cc(-c2ccnc3[nH]ccc23)c(-c2ccc(NC(=O)N3CCOCC3)cc2)n1
title product
Rendement 50.0%
CCn1cc(-c2ccnc3[nH]ccc23)c(-c2ccc(NC(=O)N3CCOCC3)cc2)n1
N-{4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-4-morpholinecarboxamide
Rendement 50.0%

Conditions de réaction

Température
50°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Extractionfollowed by extraction with (3×3 mL) ethyl acetate
  2. 2
    SéchageThe combined organic layers were dried over sodium sulfate
  3. 3
    Concentrationconcentrated in vacuo
  4. 4
    AutrePurification of the residue by Gilson reverse phase HPLC

Mode opératoire

A solution of 4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]aniline (0.19 mmol) in dichloromethane (1 mL) was treated with triethylamine (0.39 mmol) and 4-morpholinecarbonyl chloride (0.39 mmol). The reaction mixture was stirred for 18 h at 50° C. and poured into water (1 mL), followed by extraction with (3×3 mL) ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC provided the title product as a yellow powder (50%). ESMS [M+H]+: 417.4

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07419988B2uspto-grants-2008_09