1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-benzyl-2-(S)-hydroxy-3-oxo-3-pyrrolidin-1-ylpropyl)amide

HRID 1693459Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1693459
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14]([C:16]([NH:18][C@@H:19]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@H:20]([OH:24])[C:21](O)=[O:22])=[O:17])[NH:13][C:10]2=[CH:11][N:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.[Cl-].[Na+].O>[CH2:25]([C@H:19]([NH:18][C:16]([C:14]1[NH:13][C:10]2=[CH:11][N:12]=[C:7]([Cl:6])[CH:8]=[C:9]2[CH:15]=1)=[O:17])[C@H:20]([OH:24])[C:21](=[O:22])[N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 111879523-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(S)-hydroxy-4-phenylbutyric acid

Produkt 1

HCID 597536795-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-benzyl-2-(S)-hydroxy-3-oxo-3-pyrrolidin-1-ylpropyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Pyrrolidine (7 μg, 0.084 mmol) was added to a solution of 3-(S)-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(S)-hydroxy-4-phenylbutyric acid (EXAMPLE 124, 30 mg, 0.080 mmol), HOBt (14 mg, 0.091 mmol), DIPEA (31 μL, 0.18 mmol) and EDCI (18 mg, 0.094 mmol) in DMF (3 mL). After stirring for 12 h the mixture was added to diluted brine (100 mL, water/brine: 1/1). Extraction with ethyl acetate (4×25 mL), washing of the combined extracts with brine (50 mL) and drying (MgSO4), gave, after concentration, a residue which was purified by preparative LCMS to give the title compound as a colourless solid. m/z (ES+)=427.31 [M+H]+; RT=3.27 min.

Aufarbeitung

  1. extractionExtraction with ethyl acetate (4×25 mL)
  2. washwashing of the combined extracts with brine (50 mL)
  3. dry with materialdrying (MgSO4)
  4. customgave
  5. concentrationafter concentration
  6. customa residue which was purified by preparative LCMS

Quellen und Nachweise

ORD-Eintrag
ord-28df90b8f389426fb8689ba65716908f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158622B2

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