Acetonitrile → HCID 66558749, compound

HRID 1474467Notes

Reaction equation

HRID 1474467 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:45])(=[O:44])[C@H:36]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[OH:37]>ClCCl>[C:35]([OH:45])(=[O:44])[C@H:36]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[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 439616(S)-mandelic acidHCID 569355771032265-57-8

Product 1

HCID 66558749HCID 66558749, compoundYield 87%

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. 1.81 g (12 mmol) L-mandelic acid was added and the solution was heated to reflux with stirring under nitrogen atmosphere. After reaction for 1 h, the resulting mixture was filtered while 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 solution was filtered, and the filter cake was dried at 40° C. under vacuum, to give the title compound as orange solid (5.02 g, 8.7 mmol, yield 87%).

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 mixture was filtered while hot, and the filtrate
  6. concentrationwas concentrated at reduced pressure to dryness
  7. additionadded to 30 ml anhydrous ethanol
  8. additiontreated under ultrasonic sound to uniform dispersion
  9. filtrationsolution was filtered
  10. customthe filter cake was dried at 40° C. under vacuum

Sources & evidence

ORD record
ord-adcae4d05f32482cbc72b144f1e3239a
Source dataset
uspto-grants-2015_04
Patent number
US09018242B2

Reaction notes

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