Hydrogen Sulfide → (4,5-Dimethoxy-2-{[4-(1-methyl(2-imidazolin-2-yl))phenyl]carbonylamino}phenyl)-n-(5-bromo(2-pyridyl))carboxamide

HRID 1181551Notes

Reaction equation

HRID 1181551 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=2[NH:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)=[O:23])=[O:10])=[N:6][CH:7]=1.S>CCN(CC)CC.N1C=CC=CC=1>[CH3:20][O:19][C:14]1[C:15]([O:17][CH3:18])=[CH:16][C:11]([C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[O:10])=[C:12]([NH:21][C:22]([C:24]2[CH:25]=[CH:26][C:27]([C:30]3[N:6]([CH3:7])[CH2:5][CH2:4][N:31]=3)=[CH:28][CH:29]=2)=[O:23])[CH:13]=1

Participants

4

Reactant 2

HCID 402Hydrogen SulfideHCID 10277543n-{2-[n-(5-Bromo(2-pyridyl))carbamoyl]4,5-dimethoxyphenyl}(4-cyanophenyl)carboxamide

Product 1

HCID 9828663(4,5-Dimethoxy-2-{[4-(1-methyl(2-imidazolin-2-yl))phenyl]carbonylamino}phenyl)-n-(5-bromo(2-pyridyl))carboxamide

Reagents, catalysts & solvents 1

HCID 22561186Pyridine triethylamineSolvent

Procedure

To a solution of compound obtained in Example 259 (100 mg, 0.20 mmol) in 10% Et3N/pyridine (10 mL) at 0° C. was bubbled dry H2S gas to saturation. The mixture was stirred at ambient temperatures overnight, and the conversion was complete. The solvent was removed to dryness, and the residue was suspended in anhydrous acetone. (10 mL), followed by addition of MeI (1 mL). The reaction mixture was refluxed for 1 hour. The solvent was removed by rotary evaporation. To the residue was added anhydrous MeOH (10 mL) and N-methylethylenediamine (1 mL). The resulting mixture was refluxed for 1 hour, concentrated and subjected to RP-HPLC purification to give the title compound. MS found for C25H24BrN5O4 (M+H)+: 538.1, 540.1.

Workup

  1. customThe solvent was removed to dryness
  2. addition(10 mL), followed by addition of MeI (1 mL)
  3. temperatureThe reaction mixture was refluxed for 1 hour
  4. customThe solvent was removed by rotary evaporation
  5. additionTo the residue was added anhydrous MeOH (10 mL) and N-methylethylenediamine (1 mL)
  6. temperatureThe resulting mixture was refluxed for 1 hour
  7. concentrationconcentrated
  8. customsubjected to RP-HPLC purification

Sources & evidence

ORD record
ord-2cfb0af5c4fa4c9a9c81bd84ffff16a0
Source dataset
uspto-grants-2007_10
Patent number
US07285565B2

Reaction notes

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