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

HRID 595442

Reaction equation

HRID 595442 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4cc06ae56bfc4f3fb1b9aef0139a49f5
Source dataset
uspto-grants-2016_01
Patent number
US09242975B2

Linked notes

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