Sodium Hydroxide → HCID 6320620, compound

HRID 1788569Notes

Reaction equation

HRID 1788569 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.C([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)C.[OH-].[Na+]>CN(C=O)C>[CH:65]1([N:64]2[C:61]3[CH:62]=[CH:63][C:58]([C:57]([OH:56])=[O:72])=[CH:59][C:60]=3[N:71]=[C:12]2[C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[NH:5][C:4]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:3][C:2]3=[O:1])[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70]1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 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 acid2×

Product 1

HCID 6320620HCID 6320620, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Oxo-2-phenyl-1,4-dihydro-quinoline-6-carboxylic acid (298.5 mg, 1.05 mmol), (Compound 481c), was dissolved in DMF (5 mL), and HATU (440 mg, 1.1 eq.) and diisopropyl ethylamine (402 μL) were added. After stirring at room temperature for 15 minutes, 3-amino-4-cyclohexylamino-benzoic acid ethyl ester (303 mg, 1.1 eq.) dissolved in 2 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. Saponification proceeded by dissolving the residue in ethanol (10 mL), adding 10 eq. of 1N NaOH solution and stirring at 40° C. for 4 hr. The ethanol was evaporated, and water was added and acidified. The resulting precipitate is purified via reverse-phase HPLC. Yield: 47 mg.

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. dissolutionby dissolving the residue in ethanol (10 mL)
  12. stirringstirring at 40° C. for 4 hr
  13. customThe ethanol was evaporated
  14. additionwater was added
  15. customThe resulting precipitate is purified via reverse-phase HPLC

Sources & evidence

ORD record
ord-6f04f0a8359e4e8fb01a48ccab0a1caa
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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