tert-Butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate → tert-Butyl 3-(5-((S)-1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)pyrrolidine-1-carboxylate

HRID 2205611Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2205611
C(OC([NH:11][C@H:12]([C:14]1[N:19]=[C:18]2[CH:20]=[CH:21][N:22]([CH3:23])[C:17]2=[CH:16][C:15]=1[C:24]1[CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH:28]=1)[CH3:13])=O)C1C=CC=CC=1>CCO.[Pd]>[NH2:11][C@H:12]([C:14]1[N:19]=[C:18]2[CH:20]=[CH:21][N:22]([CH3:23])[C:17]2=[CH:16][C:15]=1[CH:24]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:25]1)[CH3:13]

Komponenten

4

Edukt 1

HCID 118214749tert-Butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

Produkt 1

HCID 118207715tert-Butyl 3-(5-((S)-1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)pyrrolidine-1-carboxylateAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
27 °C

Versuchsvorschrift

A mixture of tert-butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (900 mg, 1.89 mmol) and Pd/C (100 mg) in EtOH (50 mL) was stirred at 27° C. for 3 hours under H2 (50 psi). The reaction mixture was subsequently filtered, and the filtrate was concentrated to dryness. The residue was purified by preparative HPLC to afford a mixture of the diastereomers of the title compound as a yellow oil (350 mg, 54%). 1H NMR (400 MHz, CDCl3) δ ppm 7.44 (d, J=6.4 Hz, 1H), 7.22 (d, J=3.2 Hz, 1H), 6.61 (d, J=3.2 Hz, 1H), 4.51 (q, J=6.4 Hz, 1H), 3.86-3.37 (m, 1H), 3.76 (s, 3H), 2.31-2.30 (m, 1H), 1.50 (s, 9H), 1.44 (d, J=6.4 Hz, 3H); ESI-MS m/z [M+H]+ calc'd for C19H28N4O2, 345. found 345.

Aufarbeitung

  1. filtrationThe reaction mixture was subsequently filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was purified by preparative HPLC
  4. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-6b4fad31638e4dcc89aac73f8b098ee9
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09371321B2

Notizen zur Reaktion

Wird geladen…