Triethylamine → HCID 18917535, compound

HRID 1940801Notes

Reaction equation

HRID 1940801 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-cef2fa6e15a14c8f9d80e31504a5016b
Source dataset
uspto-grants-1997_12
Patent number
US05700796

Reaction notes

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