Triethylamine → HCID 18917535, compound

HRID 1735246Notes

Reaction equation

HRID 1735246 reaction equation
[CH:1]1[N:5]2[C:6]3[C:11]([NH:12][CH2:13][C:4]2=[CH:3][CH:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.C(N(CC)CC)C.[F:21][C:22]1[CH:23]=[CH:24][C:25]([CH3:40])=[C:26]([CH:39]=1)[C:27]([NH:29][C:30]1[N:35]=[CH:34][C:33]([C:36](Cl)=[O:37])=[CH:32][CH:31]=1)=[O:28]>ClCCl.O>[CH:1]1[N:5]2[C:6]3[C:11]([N:12]([C:36]([C:33]4[CH:32]=[CH:31][C:30]([NH:29][C:27](=[O:28])[C:26]5[CH:39]=[C:22]([F:21])[CH:23]=[CH:24][C:25]=5[CH3:40])=[N:35][CH:34]=4)=[O:37])[CH2:13][C:4]2=[CH:3][CH:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 118051814,5-Dihydropyrrolo[1,2-a]quinoxalineHCID 155082506-(5-Fluoro-2-methylbenzoyl)aminopyridine-3-carbonyl chloride

Product 1

HCID 18917535HCID 18917535, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a chilled (0° C.) solution of 0.341 g of 4,5-dihydropyrrolo [1,2-a]quinoxaline and 1.11 ml of triethylamine in 5 ml of dichloromethane is added 1.17 g of 6-[(5-fluoro-2-methylbenzoyl)amino]pyridine-3-carbonyl chloride. The mixture is stirred under argon at room temperature for 16 hours. The mixture is diluted with 50 ml of dichloromethane and 20 ml of water and the organic layer is separated. The organic layer is washed with 20 ml each of 1M NaHCO3 and brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the pad washed with dichloromethane. The filtrate is concentrated and the residue purified on silica gel prep-plates with ethyl acetate-hexane (1:1) as solvent to give a solid. The solid is crystallized from ethyl acetate to give 0.38 g of crystals, m.p. 190°-196° C.

Workup

  1. customthe organic layer is separated
  2. washThe organic layer is washed with 20 ml each of 1M NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. washthe pad washed with dichloromethane
  6. concentrationThe filtrate is concentrated
  7. customthe residue purified on silica gel prep-plates with ethyl acetate-hexane (1:1) as solvent
  8. customto give a solid
  9. customThe solid is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-ba32600293504844bef2c48077e7e6b9
Source dataset
uspto-grants-1996_07
Patent number
US05536718

Reaction notes

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