Maleic Acid → HCID 24899060, compound

HRID 2382585Notes

Reaction equation

HRID 2382585 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:13][C:12]2[CH:14]=[C:15]([CH2:18][CH:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])[CH:16]=[CH:17][C:11]=2[O:10][CH2:9][CH2:8]1.[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30]>CO>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:13][C:12]2[CH:14]=[C:15]([CH2:18][CH:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])[CH:16]=[CH:17][C:11]=2[O:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 24899056HCID 24899056, compound

Product 1

HCID 24899060HCID 24899060, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5-(4-Pyridine-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-7-ylmethyl)-thiazolidine-2,4-dione [compound of Example 4] (260.2 mg, 0.730 mmol) was dissolved in methanol (20 mL). To this solution, maleic acid (85 mg, 0.730 mmol) was added under stirring at room temperature to give a turbid solution. On warming to 40° C., both the components dissolved completely. It was then diluted with methanol (10 mL) and stirred overnight. The reaction mixture was filtered and concentrated to give a yellow oil. The oil was dried under high vacuum at 40° C. for 2 hours to give a yellow crystalline solid.

Workup

  1. customto give a turbid solution
  2. temperatureOn warming to 40° C.
  3. dissolutionthe components dissolved completely
  4. stirringstirred overnight
  5. filtrationThe reaction mixture was filtered
  6. concentrationconcentrated
  7. customto give a yellow oil
  8. customThe oil was dried under high vacuum at 40° C. for 2 hours
  9. customto give a yellow crystalline solid

Sources & evidence

ORD record
ord-a35f1044b549468bb0c4b76add9003ee
Source dataset
uspto-grants-2012_09
Patent number
US08263587B2

Reaction notes

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