Reaktion #1933992

ord-7451cc8c84e042bba08cf220a5517de5

Reaktionsgleichung

CC(=O)N1CC=C(c2cccnc2O[C@H]2C[C@@H](Nc3nc4ccccc4s3)C2)CC1
1-(4-(2-(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutoxy)pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone
Cc1cc2nc3c(=O)[nH]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C
E101
→
CC(=O)N1CCC(c2cccnc2O[C@H]2C[C@@H](Nc3nc4ccccc4s3)C2)CC1
1-(4-(2-(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutoxy)pyridin-3-yl)piperidin-1-yl)ethanone

Edukte

CC(=O)N1CC=C(c2cccnc2O[C@H]2C[C@@H](Nc3nc4ccccc4s3)C2)CC1
1-(4-(2-(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutoxy)pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone
Cc1cc2nc3c(=O)[nH]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C
E101

Reagenzien

[OH-].[OH-].[Pd+2]
palladium hydroxide
[Pd]
Pd

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe cooled reaction
  2. 2
    Filtrationwas filtered via a pad of Celite®
  3. 3
    Einengenthe filtrate was concentrated in vacuo
  4. 4
    Sonstigepurified via flash column chromatography (20% EtOAc/Hexanes to 100% EtOAc)

Vorschrift

A solution of 1-(4-(2-(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutoxy)pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone (0.12 g, 0.28 mmol) in ethanol (2 mL) was added palladium hydroxide, 20 wt. % Pd (dry basis) on carbon, wet, Degussa type E101 NE/W (0.039 g, 0.056 mmol) and hydrogenated (double-walled balloon pressure) at 50° C. for 3 days. The cooled reaction was filtered via a pad of Celite®, and the filtrate was concentrated in vacuo and purified via flash column chromatography (20% EtOAc/Hexanes to 100% EtOAc) to afford 1-(4-(2-(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutoxy)pyridin-3-yl)piperidin-1-yl)ethanone as a white solid. [M+1]=423.0. IC50 (uM): 0.001566.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08952037B2uspto-grants-2015_02