Maleic Acid → HCID 86654537, compound

HRID 2382592Notes

Reaction equation

HRID 2382592 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]([CH:18]=[C: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.ClCCl>[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]([CH:18]=[C: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 74348952HCID 74348952, compound

Product 1

HCID 86654537HCID 86654537, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a mixture of 5-(4-Pyridin-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-7-ylmethylene)-thiazolidine-2,4-dione [compound of Example 3] (35.3 mg, 0.1 mmol) and maleic acid (11.6 mg, 0.1 mmol) in a 100 mL two necked round bottomed flask was added 30 mL methanol:dichloromethane (2:1). The mixture was heated until a clear solution was obtained. The solution was stirred overnight (16 hours) and concentrated to give a solid which was recrystallized from methanol:dichloromethane:petroleum ether to give crystals of 5-(4-Pyridin-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-7-ylmethylene)-thiazolidine-2,4-dione maleate. mp: 224-226° C.

Workup

  1. temperatureThe mixture was heated until a clear solution
  2. customwas obtained
  3. concentrationconcentrated
  4. customto give a solid which
  5. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-d648df856e2545b3b83539dce841ff26
Source dataset
uspto-grants-2012_09
Patent number
US08263587B2

Reaction notes

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