HCID 395229, compound → 1,3-Benzothiazol-2-yl(pyrimidin-4-yl)acetonitrile

HRID 2377593Notes

Reaction equation

HRID 2377593 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:13]1[CH:18]=[CH:17][N:16]=[C:15](Cl)[N:14]=1)[C:11]#[N:12].C([O-])(=O)C.[Na+]>C(O)(=O)C.[Pd]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][N:14]=1)[C:11]#[N:12]

Participants

5

Reactant 2

HCID 395229HCID 395229, compoundHCID 517045Sodium Acetate

Product 1

HCID 179068071,3-Benzothiazol-2-yl(pyrimidin-4-yl)acetonitrileYield 13.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1 (0.1 g, 0.35 mmol) in acetic acid was added sodium acetate (29 mg, 0.35 mmol) and palladium on charcoal (20 mg). The suspension was heated up to 70° C. under hydrogen at 3.5 bar for 3 h. After cooling to r.t., the suspension was filtered through celite and the acetic acid evaporated. The bright yellow powder was taken up in ethyl acetate and aqueous sodium hydroxide 10%. After 3 extractions the organic phases were thoroughly washed with brine then dried over MgSO4 and concentrated to dryness. After purification by preparative HPLC and drying under vacuum at 50° C., 12 mg (13%) of the title compound were obtained as a yellow powder.

Workup

  1. temperatureAfter cooling to r.t.
  2. filtrationthe suspension was filtered through celite
  3. customthe acetic acid evaporated
  4. extractionAfter 3 extractions the organic phases
  5. washwere thoroughly washed with brine
  6. dry with materialthen dried over MgSO4
  7. concentrationconcentrated to dryness
  8. customAfter purification by preparative HPLC
  9. customdrying under vacuum at 50° C.

Sources & evidence

ORD record
ord-eb1e3da77b1a47679dbc3f0f04feb804
Source dataset
uspto-grants-2008_12
Patent number
US07470686B2

Reaction notes

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