Dichloromethane → HCID 69154117, compound

HRID 2373195Notes

Reaction equation

HRID 2373195 reaction equation
[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[N+:19]([O-])=O)(=[O:3])[CH3:2].C(OC(=O)[NH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33](N)=[CH:32][CH:31]=1)(C)(C)C.FC(F)(F)C(O)=O.ClCCl>C(O)C>[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[NH:19][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][NH2:28])=[CH:31][CH:32]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

Product 1

HCID 69154117HCID 69154117, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 100 mg (0.348 mmol) of 5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one (Dal Piaz, V et al, J. Med. Chem. 1997, 40, 1417) in ethanol (6 ml), (4-aminobenzyl)carbamic acid tert-butyl ester (Gallo-Rodriguez, C et al J. Med. Chem. 1994, 37(5), 636-46) (1.16 mg, 0.52 mmol) was added portionwise. The resulting mixture was stirred at room temperature for 1 h. The precipitate thus formed was collected by filtration and washed with diethylether. Then it was solved in dichloromethane (1 mL) and trifluoroacetic acid (0.23 mL, 3.03 mmol) was added dropwise. The final mixture was stirred at room temperature for 20 minutes. Some more dichloromethane was added and this solution was washed with saturated K2CO3 solution until pH 6. The organic layer was dried and solvent removed to yield 70 mg (54% yield) of the title compound.

Workup

  1. customThe precipitate thus formed
  2. filtrationwas collected by filtration
  3. washwashed with diethylether
  4. washthis solution was washed with saturated K2CO3 solution until pH 6
  5. customThe organic layer was dried
  6. customsolvent removed

Sources & evidence

ORD record
ord-a80314914e0d4925acf959483cc588ba
Source dataset
uspto-grants-2008_12
Patent number
US07459453B2

Reaction notes

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