L-Tartaric acid → HCID 49856396, compound

HRID 705508Notes

Reaction equation

HRID 705508 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[N:12]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=[CH:9]3)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:22]([OH:31])(=[O:30])[C@@H:23]([C@H:25]([C:27]([OH:29])=[O:28])[OH:26])[OH:24]>[N+](C)([O-])=O>[C:27]([C@@H:25]([C@H:23]([C:22]([OH:31])=[O:30])[OH:24])[OH:26])([OH:29])=[O:28].[N:1]1([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[N:12]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=[CH:9]3)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 248987326-(1H-Imidazol-1-yl)-2-phenylquinazoline

Product 1

HCID 49856396HCID 49856396, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
60 °C

Procedure

6-(1H-Imidazol-1-yl)-2-phenylquinazoline, 500 mg (1.8 mmol), is dissolved in 50 mL of nitromethane at reflux, with stirring and under a stream of nitrogen, 300 mg of L-tartaric acid are added, the mixture is stirred for a few minutes, it is filtered under nitrogen and the filtrate is heated to 60° C., evaporating off the solvent under a gentle vacuum, with stirring and under a stream of nitrogen, down to about ½ of the volume, and is then allowed to cool to 0° C. under nitrogen, stirred overnight at room temperature, and then filtered and dried at 30° C., 20 mmHg, for 24 hours. 520 mg of product are obtained in the form of yellow crystals, KF<0.5%, Calculated for C17H12N4.C4H6O6: C, 59.71; H, 4.30; N, 13.26. found: C, 59.76; H, 4.34; N, 13.22. XRPD form D. Form D heated at 40° C., 85% RH for 7 days gives an XRPD corresponding to form A, and an amorphous product when heated at 90° C. for 12 hours.

Workup

  1. temperatureat reflux
  2. additionare added
  3. filtrationit is filtered under nitrogen
  4. customevaporating off the solvent under a gentle vacuum
  5. stirringwith stirring and under a stream of nitrogen, down to about ½ of the volume
  6. temperatureto cool to 0° C. under nitrogen
  7. stirringstirred overnight at room temperature
  8. filtrationfiltered
  9. customdried at 30° C.

Sources & evidence

ORD record
ord-b0c15501b8924fa383520e424872ad92
Source dataset
uspto-grants-2015_11
Patent number
US09174966B2

Reaction notes

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