Acetonitrile → HCID 62705059, compound

HRID 1474456Notes

Reaction equation

HRID 1474456 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:43])(=[O:42])[C@H:36]([CH2:38][C:39]([OH:41])=[O:40])[OH:37]>ClCCl>[C:35]([OH:43])(=[O:42])[C@H:36]([CH2:38][C:39]([OH:41])=[O:40])[OH:37].[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 222656L-Malic AcidHCID 569355771032265-57-8

Product 1

HCID 62705059HCID 62705059, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8.49 g (20 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 500 ml acetonitrile and 90 ml dichloromethane. The mixture was treated under ultrasonic sound to uniform dispersion. 3.22 g (24 mmol) L-malic 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, and the resulting product was added to 60 ml anhydrous ethanol and treated under ultrasonic sound to uniform dispersion. Then the solution was filtered, and the filter cake was dried at 40° C. under vacuum, to give the title compound as yellow solid (10.39 g, 18.6 mmol, yield 93%).

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. additionthe resulting product was added to 60 ml anhydrous ethanol
  8. additiontreated under ultrasonic sound to uniform dispersion
  9. filtrationThen the solution was filtered
  10. customthe filter cake was dried at 40° C. under vacuum

Sources & evidence

ORD record
ord-32a0763cbe514b86b2155c1b967f7514
Source dataset
uspto-grants-2015_04
Patent number
US09018242B2

Reaction notes

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