Fumaric Acid → HCID 131727630, compound

HRID 733112Notes

Reaction equation

HRID 733112 reaction equation
[CH3:1][C:2]1([CH3:30])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3([C:26]([OH:28])=[O:27])[CH2:25][CH2:24][CH2:23]3)[CH2:17][CH2:16]2)=[O:12])[C:3]1=[O:29].[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35]>C1COCC1>[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35].[CH3:1][C:2]1([CH3:30])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3([C:26]([OH:28])=[O:27])[CH2:25][CH2:24][CH2:23]3)[CH2:17][CH2:16]2)=[O:12])[C:3]1=[O:29].[CH3:1][C:2]1([CH3:30])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3([C:26]([OH:28])=[O:27])[CH2:25][CH2:24][CH2:23]3)[CH2:17][CH2:16]2)=[O:12])[C:3]1=[O:29]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 11611338HCID 11611338, compound

Product 1

HCID 131727630HCID 131727630, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-{[4-({[(3,3-Dimethyl-2-oxo-2,3-dihydro-1h-indol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}cyclobutanecarboxylic acid (2.09 g, 5.04 mmol, Example 9) was dissolved with THF (25 mL) at 60° C. Fumaric acid (293 mg, 2.52 mmol) was added to the solution. The mixture was concentrated until 12.5 mL. It was cooled to room temperature, and stirred for 1 h. After filtration, the obtained solid was washed with THF (3 mL), and dried in vacuo. The desired compound was obtained as a white solid (2.02 g, 85%).

Workup

  1. concentrationThe mixture was concentrated until 12.5 mL
  2. filtrationAfter filtration
  3. washthe obtained solid was washed with THF (3 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-989e9106fbb1440385988d65c79b03e4
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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