Benzoic Acid → N'-benzoyl-6-chloro-4-(isopropylamino)nicotinohydrazide

HRID 595517

Reaktionsgleichung

Reaktionsgleichung von HRID 595517
[Cl:1][C:2]1[CH:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][N:3]=1.[C:16](O)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:16]([NH:9][NH:8][C:6](=[O:7])[C:5]1[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])=[CH:11][C:2]([Cl:1])=[N:3][CH:4]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

7

Edukt 5

HCID 243Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 896896686-Chloro-4-(isopropylamino)nicotinohydrazide

Produkt 1

HCID 89689702N'-benzoyl-6-chloro-4-(isopropylamino)nicotinohydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Chloro-4-(isopropylamino)nicotinohydrazide (10) (500 mg, 2.1 mmol) and benzoic acid (2.1 mmol, 1 equiv.) were dissolved in DMF (10 mL). EDC.HCl (1.5 equiv.), DIPEA (3 equiv.) and HOBT (1.5 equiv.) were added to the reaction mixture and stirred at room temperature for 5 h. The reaction mass was concentrated under reduced pressure to remove excess of solvent present. Diluted the residue with EtOAc and washed water followed by brine solution. The organic layer was collected, dried over Na2SO4, filtered and concentrated to get N′-benzoyl-6-chloro-4-(isopropylamino)nicotinohydrazide.

Aufarbeitung

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. customto remove excess of solvent present
  3. additionDiluted the residue with EtOAc
  4. washwashed water
  5. customThe organic layer was collected
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-72967ccf59bc47f79d31764949a1cb39
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242976B2

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