Diisopropylethylamine → HCID 58914773, compound

HRID 2242022Notes

Reaction equation

HRID 2242022 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)[C:7]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:6]1.Cl[C:27]1[N:32]=[C:31]([NH2:33])[C:30]([N+:34]([O-:36])=[O:35])=[CH:29][CH:28]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[NH2:33][C:31]1[N:32]=[C:27]([NH:1][CH2:2][CH2:3][CH2:4][N:5]2[CH:9]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=3)[C:7]([NH:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])=[CH:6]2)[CH:28]=[CH:29][C:30]=1[N+:34]([O-:36])=[O:35]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 58914793HCID 58914793, compound

Product 1

HCID 58914773HCID 58914773, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

N-[1-(3-aminopropyl)-4-(4-ethylphenyl)pyrrol-3-yl] (tert-butoxy)carboxamide (1 eq) and 6-chloro-3-nitro-2-pyridylamine (1.2 eq) were dissolved in DMA with stirring under argon at rt. Hünig's Base (1.5 eq) was added to the clear dark brown solution which was heated to 60° C. for 12 hours until completion was determined by LC/MS and TLC, eluting with EtOAc/Hexane (3:2, v/v) (Rf=0.3). EtOAc was added to the reaction mixture which was then washed with water, brine, dried (Na2SO4), filtered, and concentrated to dryness to give the crude brown product. The brown residue was purified by silica column chromatography eluting with EtOAc/Hexane (24:26, v/v). After collecting the purified fractions and concentrating, the product was isolated as a light yellow solid (75% yield).

Workup

  1. temperaturewas heated to 60° C. for 12 hours until completion
  2. washeluting with EtOAc/Hexane (3:2
  3. additionEtOAc was added to the reaction mixture which
  4. washwas then washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customto give the crude brown product
  9. customThe brown residue was purified by silica column chromatography
  10. washeluting with EtOAc/Hexane (24:26
  11. customAfter collecting the purified fractions
  12. concentrationconcentrating

Sources & evidence

ORD record
ord-7558f034bd8a437da482f1a18ca21226
Source dataset
uspto-grants-2010_03
Patent number
US07671049B2

Reaction notes

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