Acetonitrile → HCID 66558587, compound

HRID 1474465Notes

Reaction equation

HRID 1474465 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:17]2[CH2:16][CH2:15][CH2:14]/[C:13](=[C:18]3/[C:19](=[O:28])[NH:20][C:21]4[C:26]/3=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)/[C:12]=2[NH:11][C:10]=1[CH3:29])=[O:8])[CH3:2].C(#N)C.[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39]>ClCCl>[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39].[CH2:30]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:17]2[CH2:16][CH2:15][CH2:14]/[C:13](=[C:18]3/[C:19](=[O:28])[NH:20][C:21]4[C:26]/3=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)/[C:12]=2[NH:11][C:10]=1[CH3:29])=[O:8])[CH3:31]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 444972Fumaric AcidHCID 569355771032265-57-8

Product 1

HCID 66558587HCID 66558587, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.25 g (10 mmol) (Z)—N-[2-(diethylamino)ethyl]-2-methyl-7-(1,2-dihydro-5-fluoro-2-oxo-3H-indol-3-ylidene)-4,5,6,7-tetrahydro-1H-indol-3-carboxamide was added to a mixture of 250 ml acetonitrile and 50 ml dichloromethane. The mixture was treated under ultrasonic sound to uniform dispersion. 1.36 g (11.7 mmol) fumaric acid was added and the solution was heated to reflux with stirring under nitrogen atmosphere. After reaction for 1 h, the resulting solution was filtered while being hot, and the filtrate was concentrated at reduced pressure to dryness, added to 30 ml anhydrous ethanol and treated under ultrasonic sound to uniform dispersion. Then the solution filtered, and the filter cake was dried at 40° C. under vacuum, to give the title compound as yellow solid (5.14 g, 9.5 mmol, yield 95%).

Workup

  1. additionThe mixture was treated under ultrasonic sound to uniform dispersion
  2. temperaturethe solution was heated
  3. temperatureto reflux
  4. customAfter reaction for 1 h
  5. filtrationthe resulting solution was filtered
  6. concentrationthe filtrate was concentrated at reduced pressure to dryness
  7. additionadded to 30 ml anhydrous ethanol
  8. additiontreated under ultrasonic sound to uniform dispersion
  9. filtrationThen the solution filtered
  10. customthe filter cake was dried at 40° C. under vacuum

Sources & evidence

ORD record
ord-46f3031f073544c49af1ef3f29f96907
Source dataset
uspto-grants-2015_04
Patent number
US09018242B2

Reaction notes

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