Sodium Hydroxide → 4-(5-Azido-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester

HRID 1887071Notizen

Reaktionsgleichung

[OH-].[Na+].N1CCC[C@H]1C(O)=O.[N-:11]=[N+:12]=[N-:13].[Na+].[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([O:28][C:29]2[C:30](I)=[C:31]3[C:36](=[CH:37][CH:38]=2)[CH:35]=[N:34][CH:33]=[CH:32]3)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CS(C)=O.[Cu]I.O>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([O:28][C:29]2[C:30]([N:11]=[N+:12]=[N-:13])=[C:31]3[C:36](=[CH:37][CH:38]=2)[CH:35]=[N:34][CH:33]=[CH:32]3)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Under argon atmosphere 40 μL (0.04 mmol) of 1 N NaOH, 4.6 mg (0.04 mmol) of L-proline, 3.8 mg of (0.02 mmol) CuI and 15.6 mg (0.24 mmol) of NaN3 were added to a solution of 91 mg (0.2 mmol) of 4-(5-iodo-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester (12) in 2 mL of DMSO. The mixture was heated to 60° C. for 18 h. NaN3, NaOH and L-proline were added in the same amounts again and the reaction was heated to 60° C. for 5 h. After cooling to room temperature water was added. The precipitate was filtered, washed with water and dried in vacuo to give 74 mg of compound 17, which was used without any additional purification.

Aufarbeitung

temperaturethe reaction was heated to 60° C. for 5 h
additionwas added
filtrationThe precipitate was filtered
washwashed with water
customdried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-dabea5ef2c044eb49b17dceb2c79c7ba
Quelldatensatz: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08501736B2

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