Diisopropylethylamine → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [2-(2-carbamoylpiperidin-1-yl)-1-(S)-(4-fluorobenzyl)-2-oxoethyl]amide

HRID 751723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751723
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([NH2:10])=[O:9].[Cl:11][C:12]1[CH:13]=[C:14]2[CH:20]=[C:19]([C:21]([NH:23][C@@H:24]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[C:25](O)=[O:26])=[O:22])[NH:18][C:15]2=[CH:16][N:17]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:8]([CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][N:2]1[C:25](=[O:26])[C@@H:24]([NH:23][C:21]([C:19]1[NH:18][C:15]2=[CH:16][N:17]=[C:12]([Cl:11])[CH:13]=[C:14]2[CH:20]=1)=[O:22])[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=1)(=[O:9])[NH2:10]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16248268Piperidine-2-carboxamide hydrochlorideHCID 597536992-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propionic acid

Produkt 1

HCID 866017695-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [2-(2-carbamoylpiperidin-1-yl)-1-(S)-(4-fluorobenzyl)-2-oxoethyl]amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of piperidine-2-carboxylic acid amide hydrochloride (Preparation 80, 24 mg, 0.17 mmol) in DMF (3 mL) was added 2-(S)-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propionic acid (EXAMPLE 230, 52 mg, 0.14 mmol), followed by HATU (65.6 mg, 0.17 mmol) and DIPEA (63 μL, 0.36 mmol), and the reaction stirred at rt for 16 h. Solvent was removed in vacuo, purification via preparative HPLC gave the title compound as an off-white powder. m/z (ES+)=472.31 [M+H]+; RT=3.19 min.

Aufarbeitung

  1. customSolvent was removed in vacuo, purification via preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cb9b20bf87f741a3b5cb569434d3d07e
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405210B2

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