Ethylenediamine → HCID 86585881, compound

HRID 2120402Notes

Reaction equation

HRID 2120402 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].C[Al](C)C.[F:9][C:10]([CH3:41])([CH3:40])[CH2:11][CH2:12][CH:13]1[C:17](=O)[O:16][CH:15]([CH:19]([NH:27][C:28]([C:30]2[CH:39]=[N:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=2)=[O:29])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:14]1>C1(C)C=CC=CC=1>[CH2:20]([CH:19]([NH:27][C:28]([C:30]1[CH:39]=[N:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=1)=[O:29])[CH:15]([OH:16])[CH2:14][CH:13]([C:17]1[NH:3][CH2:2][CH2:1][N:4]=1)[CH2:12][CH2:11][C:10]([F:9])([CH3:41])[CH3:40])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 16682925TrimethylaluminumHCID 76502387HCID 76502387, compound

Product 1

HCID 86585881HCID 86585881, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of ethylenediamine (0.040 mL, 0.598 mmol) in toluene (2 mL) at −10° C. was added trimethylaluminum (2.0 M in hexanes, 0.300 mL, 0.600 mmol) and stirred for 15 minutes. A solution of quinoxaline-2-carboxylic acid {1-[4-(3-fluoro-3-methyl-butyl)-5-oxo-tetrahydro-furan-2-yl]-2-phenyl-ethyl}-amide (250 mg, 0.556 mmol) in toluene (3 mL) was then added and the reaction warmed to ambient temperature, then heated to reflux for 3 hours. The reaction was cooled to ambient temperature and quenched carefully with water (1 mL). The solution was diluted with methylene chloride and methanol and then filtered, washing the filtrate with methanol. The organics were concentrated and the crude product was purified by chromatography on silica gel to give the title compound (74 mg, 17%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. temperatureThe reaction was cooled to ambient temperature
  4. customquenched carefully with water (1 mL)
  5. additionThe solution was diluted with methylene chloride and methanol
  6. filtrationfiltered
  7. washwashing the filtrate with methanol
  8. concentrationThe organics were concentrated
  9. customthe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e7ff03d34a6145f39ee77be2ee2fde31
Source dataset
uspto-grants-2004_02
Patent number
US06689886B2

Reaction notes

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