1-Hydroxybenzotriazole → N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide

HRID 1921292Notes

Reaction equation

HRID 1921292 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]([C:16]([OH:18])=O)=[CH:10]1.[NH2:19][C:20]1[CH:21]=[C:22]([CH:29]=[CH:30][C:31]=1[CH3:32])[C:23]([NH:25][CH:26]1[CH2:28][CH2:27]1)=[O:24].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O.CCN(CC)CC>[CH:26]1([NH:25][C:23]([C:22]2[CH:29]=[CH:30][C:31]([CH3:32])=[C:20]([NH:19][C:16]([C:11]3[CH:12]=[CH:13][C:14](=[O:15])[N:9]([C:3]4[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[CH:10]=3)=[O:18])[CH:21]=2)=[O:24])[CH2:28][CH2:27]1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 119838543-amino-N-cyclopropyl-4-methylbenzamideHCID 655011901-(2,6-Dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

Product 1

HCID 59234669N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamideYield 66.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid (56 mg) in DMF (0.76 mL) were added 3-amino-N-cyclopropyl-4-methylbenzamide (45 mg), WSC—HCl (57 mg), HOBt (35 mg) and Et3N (27 mg), and the mixture was stirred under a nitrogen atmosphere at room temperature for 16 hr. The reaction mixture was diluted with EtOAc (2 mL), washed with water (4 mL×2) and brine successively, dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by preparative thin layer chromatography eluting with 10% MeOH in CH2Cl2 to give N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide (60 mg).

Workup

  1. washwashed with water (4 mL×2) and brine successively
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography
  6. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-4cc668a498dc477185fafd0183ef0af1
Source dataset
uspto-grants-2012_05
Patent number
US08173684B2

Reaction notes

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