1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-benzyl-3-(3,4-dihydroxypyrrolidin-1-yl)-2-(S)-hydroxy-3-oxopropyl]amide

HRID 1693460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1693460
[OH:1][C@H:2]1[C@@H:6]([OH:7])[CH2:5][NH:4][CH2:3]1.[Cl:8][C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([C:18]([NH:20][C@@H:21]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:22]([OH:26])[C:23](O)=[O:24])=[O:19])[NH:15][C:12]2=[CH:13][N:14]=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>[CH2:27]([C@H:21]([NH:20][C:18]([C:16]1[NH:15][C:12]2=[CH:13][N:14]=[C:9]([Cl:8])[CH:10]=[C:11]2[CH:17]=1)=[O:19])[C@H:22]([OH:26])[C:23]([N:4]1[CH2:5][CH:6]([OH:7])[CH:2]([OH:1])[CH2:3]1)=[O:24])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 111879523-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(S)-hydroxy-4-phenylbutyric acidHCID 13329882(3R,4S)-pyrrolidine-3,4-diol

Produkt 1

HCID 866017675-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-benzyl-3-(3,4-dihydroxypyrrolidin-1-yl)-2-(S)-hydroxy-3-oxopropyl]amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

cis-3,4-Dihydroxypyrrolidine (Preparation 23, 9 mg, 0.087 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+)=459.29 [M+H]+; RT=2.87 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-0d66f6be66344f72a1152391701640b8
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158622B2

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