Glyoxal → HCID 18355008, compound

HRID 429679Notes

Reaction equation

HRID 429679 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([NH:11][C:12]1[CH:43]=[CH:42][C:15]([C:16]([N:18]([CH3:41])[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=2[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([N:34]2[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]2)=[O:33])=[O:17])=[CH:14][C:13]=1[O:44][CH3:45])=[O:10].[CH:46]([CH:48]=O)=O.S([O-])(O)=O.[Na+]>C(O)C.C(Cl)(Cl)Cl>[CH3:45][O:44][C:13]1[CH:14]=[C:15]([CH:42]=[CH:43][C:12]=1[NH:11][C:9]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:2]=1[N:1]=[CH:46][CH:48]=[N:8]2)=[O:10])[C:16]([N:18]([CH3:41])[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([N:34]1[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]1)=[O:33])=[O:17]

Participants

6

Reactant 3

HCID 7860GlyoxalHCID 183547944-(2,3-diaminophenyl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamideHCID 23665763Sodium Bisulfite

Product 1

HCID 18355008HCID 18355008, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 4-(2,3-diaminophenyl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (200 mg), glyoxal (47 mg) and sodium hydrogen sulfite (169 mg) in ethanol (15 ml) was refluxed for 5 hours. The solution was diluted with chloroform (30 ml) and the solution was washed with water and brine. The organic solution was dried over magnesium sulfate and the solvent was evaporated in vacuo to give an oil. The crude product was purified by silica gel column (1% methanol in chloroform) to give 3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-4-(quinoxalin-5-yl)carbonylaminobenzamide (131 mg).

Workup

  1. temperaturewas refluxed for 5 hours
  2. washthe solution was washed with water and brine
  3. dry with materialThe organic solution was dried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customto give an oil
  6. customThe crude product was purified by silica gel column (1% methanol in chloroform)

Sources & evidence

ORD record
ord-58589adafe1e42c2ba0160d825d6f7c6
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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