1-Hydroxybenzotriazole → 5-({1-[2-oxo-2-(4-phenylethynyl-piperidin-1-yl)-ethyl]-pyrrolidine-3-carbonyl}-amino)-1H-indazole-3-carboxylic acid methylamide

HRID 1038045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038045
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:15]([CH:17]3[CH2:21][CH2:20][N:19]([CH2:22][C:23]([OH:25])=O)[CH2:18]3)=[O:16])[CH:12]=2)[NH:7][N:6]=1)=[O:4].[C:26]1([C:32]#[C:33][CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CCN(C(C)C)C(C)C>>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:15]([CH:17]3[CH2:21][CH2:20][N:19]([CH2:22][C:23](=[O:25])[N:37]4[CH2:38][CH2:39][CH:34]([C:33]#[C:32][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH2:35][CH2:36]4)[CH2:18]3)=[O:16])[CH:12]=2)[NH:7][N:6]=1)=[O:4]

Komponenten

6

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 179869654-(Phenylethynyl)piperidineHCID 57685850[3-(3-methylcarbamoyl-1H-indazol-5-ylcarbamoyl)-pyrrolidin-1-yl]-acetic acid

Produkt 1

HCID 576864715-({1-[2-oxo-2-(4-phenylethynyl-piperidin-1-yl)-ethyl]-pyrrolidine-3-carbonyl}-amino)-1H-indazole-3-carboxylic acid methylamideAusbeute 24 %

Versuchsvorschrift

A solution of [3-(3-methylcarbamoyl-1H-indazol-5-ylcarbamoyl)-pyrrolidin-1-yl]-acetic acid (0.13 mmols), 4-phenylethynyl-piperidine (0.13 mmols), 1-hydroxybenztriazole (18 mg, 0.13 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCl) (27 mg, 0.14 mmol) and DIEA (45 μl, 0.26 mmols) was stirred overnight and directly subjected to purification by reversed phase HPLC to obtain 16 mg of the title product.

Aufarbeitung

  1. customdirectly subjected to purification by reversed phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ff139f88408d43e38894516ab3a183fc
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546404B2

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