Diisopropylethylamine → HCID 86600381, compound

HRID 1788573Notes

Reaction equation

HRID 1788573 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12](O)=O)[CH:10]=2)[NH:5][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH2:54]([O:56][C:57](=[O:72])[C:58]1[CH:63]=[CH:62][C:61]([NH:64][CH:65]2[CH2:70][CH2:69][CH2:68][CH2:67][CH2:66]2)=[C:60]([NH2:71])[CH:59]=1)[CH3:55]>CN(C=O)C>[CH2:54]([O:56][C:57]([C:58]1[CH:63]=[CH:62][C:61]2[N:64]([CH:65]3[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70]3)[C:12]([C:9]3[CH:10]=[C:11]4[C:6](=[CH:7][CH:8]=3)[NH:5][C:4]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:3][C:2]4=[O:1])=[N:71][C:60]=2[CH:59]=1)=[O:72])[CH3:55]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4068248Ferrostatin-1HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 134215954-Oxo-2-phenyl-1,4-dihydroquinoline-6-carboxylic acid

Product 1

HCID 86600381HCID 86600381, compoundYield 800.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Oxo-2-phenyl-1,4-dihydro-quinoline-6-carboxylic acid (2.78 g, 1.05 mmol) was dissolved in DMF (50 mL), and HATU (1.1 eq.) and diisopropyl ethylamine (2.2 eq, 402 μL) were added. After stirring at room temperature for 15 minutes, 3-amino-4-cyclohexylamino-benzoic acid ethyl ester (2.89 g, 1.1 eq.) dissolved in 20 mL DMF was added. After stirring overnight, the reaction was evaporated, dissolved in ethyl acetate and washed with water and brine, dried with sodium sulfate, evaporated and dried overnight. The product was then refluxed in acetic acid for 4 hr, evaporated to dryness, and coevaporated 2 more times with toluene. The product was recrystallized from methanol to give 4.13 g of product.

Workup

  1. additionwas added
  2. stirringAfter stirring overnight
  3. customthe reaction was evaporated
  4. dissolutiondissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried with sodium sulfate
  7. customevaporated
  8. customdried overnight
  9. temperatureThe product was then refluxed in acetic acid for 4 hr
  10. customevaporated to dryness
  11. customThe product was recrystallized from methanol

Sources & evidence

ORD record
ord-92ddba25f3974eceba02eade2621de1b
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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