L-Tartaric acid → HCID 49856396, compound

HRID 705507Notes

Reaction equation

HRID 705507 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]>C(#N)C>[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 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

6-(1H-Imidazol-1-yl)-2-phenylquinazoline, 50 mg (0.18 mmol), is suspended in 4 mL of acetonitrile, the mixture is then heated at reflux and 30 mg of L-tartaric acid are added, the suspension is heated at reflux for a further 30 min, it is filtered and then cooled to 0° C., and the resulting suspension is stirred at 25° C. for three days and then filtered and dried at 20° C., 20 mmHg, for 12 hours. 30 mg of product are obtained in the form of yellow crystals, KF=14.67%, Calculated for C17H12N4.C4H6O6.4H2O: C, 51.01; H, 5.30; N, 11.33. found: C, 50.64; H, 5.41; N, 11.28. XRPD form B. Form B heated at 40° C., 85% RH for 7 days is stable (XRPD), but gives rise to the amorphous form when heated at 90° C. for 12 hours.

Workup

  1. temperaturethe mixture is then heated
  2. temperatureat reflux
  3. temperaturethe suspension is heated
  4. temperatureat reflux for a further 30 min
  5. filtrationit is filtered
  6. filtrationfiltered
  7. customdried at 20° C.
  8. wait20 mmHg, for 12 hours

Sources & evidence

ORD record
ord-a9418afe15db41a3ab3b89e68939aec8
Source dataset
uspto-grants-2015_11
Patent number
US09174966B2

Reaction notes

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