Hydrazine hydrate (1:1) → (3S*,5R*)-3-(2-Amino-ethylamino)-5-{cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1698367Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698367
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([NH:14][CH2:15][CH2:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:11][C@@H:10]([C:28](=[O:48])[N:29]([CH:45]2[CH2:47][CH2:46]2)[CH2:30][C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])[CH:32]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@H:10]([C:28](=[O:48])[N:29]([CH:45]2[CH2:47][CH2:46]2)[CH2:30][C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])[CH:32]=2)[CH2:11][C@H:12]([NH:14][CH2:15][CH2:16][NH2:17])[CH2:13]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 69066246(3R*,5S*)-3-{Cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylamino]-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 69066278(3S*,5R*)-3-(2-Amino-ethylamino)-5-{cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of (3R*,5S*)-3-{Cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylamino]-piperidine-1-carboxylic acid tert-butyl ester (160 mg, 0.24 mmol) and hydrazine monohydrate (18 uL, 0.37 mmol) in EtOH is stirred at 60° C. After 6 h, the reaction mixture is cooled down to room temperature. The solution is filtered through celite pad and the solvent is evaporated in vacuo to afford the title compound as yellow material. MS: 528 [M+H]+; tR (HPLC, ACQUITY UPLC™ BEH C18 1.7 μm, 50×2.1 mm; 5% CH3CN+0.1% TFA/H2O+0.1% TFA for 0.5 min then 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 1.5 min, flow 0.5 ml/min): 2.93 min.

Aufarbeitung

  1. temperaturethe reaction mixture is cooled down to room temperature
  2. filtrationThe solution is filtered through celite pad
  3. customthe solvent is evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f9758aa7017546e99ad0539f800d3d5f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163773B2

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