2-Chloro-1,1,1-triethoxyethane → HCID 68520851, compound

HRID 2246453Notes

Reaction equation

HRID 2246453 reaction equation
[NH2:1][C:2]1[C:3]([C:19]#[N:20])=[N:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[CH:6][C:7]=1[NH2:8].[Cl:21][CH2:22][C:23](OCC)(OCC)OCC.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(#N)C>[Cl:21][CH2:22][C:23]1[NH:8][C:7]2[CH:6]=[C:5]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[CH:10]=3)[N:4]=[C:3]([C:19]#[N:20])[C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 3059222-Chloro-1,1,1-triethoxyethaneHCID 2733225Ytterbium triflateHCID 58938115HCID 58938115, compound

Product 1

HCID 68520851HCID 68520851, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3,4-diamino-6-(3-trifluoromethyl-phenyl)-pyridine-2-carbonitrile (1.6 g) and 2-chloro-1,1,1-triethoxyethane (3.41 g,) in acetonitrile (40 ml) was added ytterbium triflate (180 mg, 5 mol %) and the mixture heated to reflux over-night. The mixture was concentrated under reduced pressure before partitioning between ethyl acetate (100 ml) and water (100 ml). The organic layer was dried over sodium sulfate and concentrated before addition of diethylether (20 ml). The precipitate was filtered and dried under a stream of air to afford the title compound. 1H NMR (MeOD) δ 8.40 (s, 1H) 8.32-8.38 (m, 2H) 8.13-8.15 (d, 2H) 7.68-7.78 (m, 2H) 4.96 (s, 2H). MS m/z 337.5, 339.1 (M+1).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux over-night
  3. concentrationThe mixture was concentrated under reduced pressure
  4. custombefore partitioning between ethyl acetate (100 ml) and water (100 ml)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated before addition of diethylether (20 ml)
  7. filtrationThe precipitate was filtered
  8. customdried under a stream of air

Sources & evidence

ORD record
ord-dc7d912debf6443db7592938893f9321
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

Loading…