Propylamine → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-benzyl-2-(R)-hydroxy-2-propylcarbamoylethyl)amide

HRID 1693461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1693461
[CH2:1]([NH2:4])[CH2:2][CH3:3].[Cl:5][C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([C:15]([NH:17][C@@H:18]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@@H:19]([OH:23])[C:20]([OH:22])=O)=[O:16])[NH:12][C:9]2=[CH:10][N:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C>[CH2:24]([C@H:18]([NH:17][C:15]([C:13]1[NH:12][C:9]2=[CH:10][N:11]=[C:6]([Cl:5])[CH:7]=[C:8]2[CH:14]=1)=[O:16])[C@@H:19]([OH:23])[C:20](=[O:22])[NH:4][CH2:1][CH2:2][CH3:3])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

7

Edukt 5

HCID 7852PropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59753553(S)-3-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-(R)-2-hydroxy-4-phenylbutyric acid

Produkt 1

HCID 597535955-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-benzyl-2-(R)-hydroxy-2-propylcarbamoylethyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

n-Propylamine (16 μL, 0.19 mmol) was added to a solution of 3-(S)-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(R)-hydroxy-4-phenylbutyric acid (EXAMPLE 44, 40 mg, 0.11 mmol), HOBt (16.4 mg, 0.11 mmol), DIPEA (41 μL, 0.24 mmol) and EDCI (25 mg, 0.13 mmol) in DMF (3 mL). After stirring for 72 h at room temperature the solvent was removed in vacuo and the remaining residue was purified by preparative LCMS to give the title compound as colourless solid. m/z (ES+)=415.34 [M+H]+; RT=3.10 min.

Aufarbeitung

  1. customwas removed in vacuo
  2. customthe remaining residue was purified by preparative LCMS

Quellen und Nachweise

ORD-Eintrag
ord-7755e580c9764a70a03e3a29b0e7d467
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158622B2

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