Water → HCID 68676607, compound

HRID 2233048Notes

Reaction equation

HRID 2233048 reaction equation
[C:1]([C:5]1[N:6]=[C:7](Cl)[C:8]2[N:9]([C:17](=[O:20])[NH:18][N:19]=2)[C:10]=1[CH:11]([OH:16])[CH2:12][CH:13]([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][NH2:30])[CH:23]=1.O>CN1CCCC1=O>[C:1]([C:5]1[N:6]=[C:7]([NH:30][CH2:29][CH2:28][C:24]2[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=2)[C:8]2[N:9]([C:17](=[O:20])[NH:18][N:19]=2)[C:10]=1[CH:11]([OH:16])[CH2:12][CH:13]([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 68677340HCID 68677340, compound

Product 1

HCID 68676607HCID 68676607, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 70 mg of the product of Step A, 34 mg of TEA and 33 mg of 2-pyridin-3-yl-ethylamine in 1-methyl-2-pyrrolidinone (1.5 mL) was heated to 80° C. After six h, the reaction mixture was cooled, poured into water and extracted with EtOAc and then 15% IPA/chloroform. The organic extracts were washed dried over sodium sulfate, filtered, and concentrated. The residue was dissolved in EtOAc and washed with water and sat. sodium chloride solution. The organic layer was dried over sodium sulfate, filtered, concentrated, and the residue was recrystallized from ether/hexanes to provide the title compound as a white solid. MS (M+H+)=397.4.

Workup

  1. temperatureAfter six h, the reaction mixture was cooled
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in EtOAc
  8. washwashed with water and sat. sodium chloride solution
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customthe residue was recrystallized from ether/hexanes

Sources & evidence

ORD record
ord-dbea19f3e0384b0495f0c88ebce68367
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

Loading…