1-Hydroxybenzotriazole → HCID 59233248, compound

HRID 1925151Notes

Reaction equation

HRID 1925151 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]([CH3:12])[C:9]([O-:11])=O)=[CH:4][CH:3]=1.[Li+].[Br:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][NH2:22])=[N:19][CH:20]=1.N1(O)C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.O>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][NH:22][C:9](=[O:11])[CH:8]([C:5]2[N:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH3:12])=[N:19][CH:20]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 115356995-Bromo-2-hydrazinopyridineHCID 59233185HCID 59233185, compound

Product 1

HCID 59233248HCID 59233248, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of lithium 2-(6-chloropyridazin-3-yl)propanoate (7.2 g, 37.4 mmol), 5-bromo-2-hydrazinylpyridine (7.03 g, 37.4 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (5.05 g, 37.4 mmol), and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (7.89 g, 41.1 mmol) in DMF (Volume: 320 ml) was stirred for 4 hrs at 25° C. The reaction was poured into H2O (2 L) and extracted with EtOAc (3×500 mL). The organic phase was dried over MgSO4, filtered, and evaporated to dryness. The resulting residue was purified by MPLC CHCl3:MeOH (9:1) to provide the title compound, N′-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)propanehydrazide 48C (5.5 g, 15.42 mmol, 41.2% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.52 (d, J=7.33 Hz, 3 H) 4.17 (d, J=7.07 Hz, 1 H) 6.52 (d, J=8.84 Hz, 1 H) 7.67 (dd, J=8.84, 2.53 Hz, 1 H) 7.87 (d, J=9.09 Hz, 1 H) 7.94 (d, J=8.84 Hz, 1 H) 8.11 (d, J=1.77 Hz, 1 H) 8.66 (d, J=1.52 Hz, 1 H) 10.20 (d, J=1.52 Hz, 1 H). ESI-MS:m/z 356.1 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×500 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe resulting residue was purified by MPLC CHCl3:MeOH (9:1)

Sources & evidence

ORD record
ord-7f956090d2a54ca5a63d906d6da42d90
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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