Maleic Acid → HCID 67531886, compound

HRID 2068748Notes

Reaction equation

HRID 2068748 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:21][C:20]2[CH2:19][CH2:18][N:17]([CH2:22][C@H:23]([OH:31])[CH2:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:16](=[O:32])[C:15]=2[C:14]=1[CH3:33].[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38]>CO>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38].[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:21][C:20]2[CH2:19][CH2:18][N:17]([CH2:22][C@H:23]([OH:31])[CH2:24][N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[C:16](=[O:32])[C:15]=2[C:14]=1[CH3:33]

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 25207322HCID 25207322, compound

Product 1

HCID 67531886HCID 67531886, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R,Z)-2-(5-Fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-hydroxy-3-morpholin-4-yl-propyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one 1 (709 mg, 1.562 mmol) and cis-butenedioic acid (217 mg, 1.874 mmol) were dissolved in 150 mL of methanol under stirring at room temperature. After stirring to mix well, the reaction mixture was heated at 40° C. in an oil bath for 20 minutes and filtered under reduced pressure. The filtrate was concentrated under reduced pressure, and 50 mL of acetonitrile was then added to the residue. Upon completion of the addition, the mixture was heated to reflux for 20 minutes. The reaction mixture was cooled down to room temperature and filtered under reduced pressure to give the title compound (R,Z)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-hydroxy-3-morpholin-4-yl-propyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one maleate 23 (811 mg, yield 91.1%) as a yellow solid.

Workup

  1. stirringAfter stirring
  2. additionto mix well
  3. temperaturethe reaction mixture was heated at 40° C. in an oil bath for 20 minutes
  4. filtrationfiltered under reduced pressure
  5. concentrationThe filtrate was concentrated under reduced pressure, and 50 mL of acetonitrile
  6. additionwas then added to the residue
  7. additionUpon completion of the addition
  8. temperaturethe mixture was heated
  9. temperatureto reflux for 20 minutes
  10. temperatureThe reaction mixture was cooled down to room temperature
  11. filtrationfiltered under reduced pressure

Sources & evidence

ORD record
ord-d4a3bf6b49f6437bba493d84946f1eba
Source dataset
uspto-grants-2012_10
Patent number
US08299069B2

Reaction notes

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