2,3-Dihydroxybutanedioic Acid → HCID 86589095, compound

HRID 1061582Notes

Reaction equation

HRID 1061582 reaction equation
Cl[CH2:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(N(CC)CC)C.[C:31]([OH:40])(=[O:39])[CH:32]([CH:34]([C:36]([OH:38])=[O:37])[OH:35])[OH:33]>CN1CCCC1=O.O>[C:36]([C@@H:34]([C@H:32]([C:31]([OH:40])=[O:39])[OH:33])[OH:35])([OH:38])=[O:37].[C:36]([C@@H:34]([C@H:32]([C:31]([OH:40])=[O:39])[OH:33])[OH:35])([OH:38])=[O:37].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH2:19][CH2:20][N:21]([CH2:2][C:3]2[NH:4][C:5]3[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=3[N:7]=2)[CH2:22][CH2:23]1

Participants

7

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 8471TriethylamineHCID 785712-ChloromethylbenzimidazoleHCID 944591-(2-Pyridyl)piperazine

Product 1

HCID 86589095HCID 86589095, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

An alternative synthesis of the title compound. 2-(Chloromethyl)benzimidazole (11.95 g, 71.7 mmol) in 50 mL of N-methylpyrrolidone was treated with 1-(2-pyridyl)piperazine (12.88 g, 78.9 mmol) at 0° C. After one hour, the mixture was treated with triethylamine (7.98 g, 78.9 mmol) and allowed to warm to room temperature. After stirring for 22 hours, the mixture was treated with (L) tartaric acid (24.8 g, 165 mmol) in 50 mL of water. After addition was complete, the mixture was heated at 80° C. for one hour and then allowed to cool to room temperature. The mixture was filtered and the solids were washed with 100 mL of ethanol. The obtained solid was dried under reduced pressure to provide 38.1 g of the title compound as a solid. Elemental analysis calc'd for C25H31N5O12: C 50.59; H, 5.26; N, 11.80; O, 32.35. Found: C, 50.48; H, 5.27; N, 11.78; O, 32.41. DSC: sharp endotherm at 206° C.

Workup

  1. additionAfter addition
  2. temperaturethe mixture was heated at 80° C. for one hour
  3. temperatureto cool to room temperature
  4. filtrationThe mixture was filtered
  5. washthe solids were washed with 100 mL of ethanol
  6. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-861048e7f83c42d3aebcc8470b4a3f99
Source dataset
uspto-grants-2005_11
Patent number
US06960589B2

Reaction notes

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