Water → Depyrazine 7,8-Dinitrophenyl Varenicline

HRID 2180080Notes

Reaction equation

HRID 2180080 reaction equation
[N+:1]([C:4]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]2[CH:11]3[CH2:18][CH:7]([CH2:8][N:9](C(=O)C(F)(F)F)[CH2:10]3)[C:6]=2[CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[Na+].[Na+].O.CO.C(Cl)Cl>CO>[N+:15]([C:14]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]2[CH:7]3[CH2:18][CH:11]([CH2:10][NH:9][CH2:8]3)[C:12]=2[CH:13]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 21226129Dichloromethane methanolHCID 218647441-(7,8-Dinitro-1,2,4,5-tetrahydro-3H-1,5-methano-3-benzazepin-3-yl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 9878181Depyrazine 7,8-Dinitrophenyl Varenicline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(4,5-Dinitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (3.7 g, 10.7 mmol) and Na2CO3 (2.3 g, 21.4 mmol) were combined in MeOH (50 mL) and H2O (20 mL) then warmed to reflux for 18 hours. The reaction was cooled, concentrated, treated with H2O and extracted with CH2Cl2 (3×50 mL) then dried through a cotton plug. After concentration, the residue was chromatographed to provide brown solids. (1.9 g, 71%). (TLC 5% MeOH/CH2Cl2 (NH3) Rf 0.36). 1H NMR (400 MHz, CDCl3) δ 7.69 (s, 2H), 3.17 (br s, 2H), 3.11 (d, J=12.6 Hz, 2H), 2.53 (m, 1H), 2.07 (d, J=11.0 Hz, 1H) GCMS m/e 249 (M+).

Workup

  1. temperatureto reflux for 18 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. additiontreated with H2O
  5. extractionextracted with CH2Cl2 (3×50 mL)
  6. customthen dried through a cotton plug
  7. concentrationAfter concentration
  8. customthe residue was chromatographed
  9. customto provide brown solids

Sources & evidence

ORD record
ord-c1477764722646ffabe095949fa43341
Source dataset
uspto-grants-2005_05
Patent number
US06887884B2

Reaction notes

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