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 1693469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1693469
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-90956ad3cb8f405f95b0f50d0398f99d
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158622B2

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