Triethylamine → Pyridine-3-carboxylic acid N'-(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)hydrazide

HRID 1362933

Reaktionsgleichung

Reaktionsgleichung von HRID 1362933
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C(N(CC)CC)C.[Cl:18][C:19]1[CH:20]=[C:21]2[CH:27]=[C:26]([C:28](O)=[O:29])[NH:25][C:22]2=[CH:23][N:24]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]2[CH:27]=[C:26]([C:28]([NH:10][NH:9][C:1]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)=[O:8])=[O:29])[NH:25][C:22]2=[CH:23][N:24]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 11112Nicotinic acid, hydrazideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 446307045-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Produkt 1

HCID 59830438Pyridine-3-carboxylic acid N'-(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)hydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of nicotinic acid hydrazide (35 mg, 0.25 mmol) in DMF (5 mL) was added triethylamine (88 μL, 0.64 mmol), 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 8, 50 mg, 0.25 mmol), HOBt (34 mg, 0.25 mmol) and EDCI (50 mg, 0.28 mmol). The mixture was allowed to stir at rt for 16 h. The solvent was removed in vacuo and the residue was partitioned between water (100 mL) and ethyl acetate (100 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to give an oil, which was purified by flash chromatography on silica gel (dichloromethane/methanol, 9/1) to give the title compound. m/z (ES+)=316 [M+H]+; RT=2.62 min.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water (100 mL) and ethyl acetate (100 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give an oil, which
  6. customwas purified by flash chromatography on silica gel (dichloromethane/methanol, 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-289e93d2f1644254a1d4659a32b7a4aa
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884112B2

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