N,N-Dimethylethylenediamine → HCID 70113029, compound

HRID 1415700Notes

Reaction equation

HRID 1415700 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[N:7]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=O)[C:8]3=[N:9]2)=[CH:4][CH:3]=1.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH2:24].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>ClCCl.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[N:7]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([NH:24][CH2:23][CH2:22][N:21]([CH3:25])[CH3:20])=[O:18])[C:8]3=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 70112915HCID 70112915, compound

Product 1

HCID 70113029HCID 70113029, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The 3-bromo-11-oxo-11H-pyrido[2,1-b]quina-zoline-6-carboxylic acid was dissolved in dichloromethane (25 ml). To the reaction mixture was added N,N-dimethyl-ethylenediamine (1 g; 0.0023 mol), followed by the BOP reagent (1 g, 0.0023 mol). The reaction mixture was stirred at room temperature for 30 minutes, diluted with water and extracted with dichloromethane. The combined organic phases were dried, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with 10% methanol/chloroform) to provide product as a yellow solid: 0.338 g.

Workup

  1. extractionextracted with dichloromethane
  2. customThe combined organic phases were dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (elution with 10% methanol/chloroform)
  6. customto provide product as a yellow solid

Sources & evidence

ORD record
ord-9a8f184198ca43dcbc1a1b463b4afbff
Source dataset
uspto-grants-1999_06
Patent number
US05908840

Reaction notes

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