Ammonium formate → 4-Amino-3-{[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amino}-benzonitrile

HRID 2064087Notes

Reaction equation

HRID 2064087 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[NH:12][CH:13]1[CH2:18][CH2:17][N:16]([CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH2:15][CH2:14]1)([O-])=O.C([O-])=O.[NH4+]>[Pd].CO>[NH2:1][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[NH:12][CH:13]1[CH2:14][CH2:15][N:16]([CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 691225114-Nitro-3-{[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amino}benzonitrile

Product 1

HCID 691227084-Amino-3-{[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amino}-benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Nitro-3-{[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amino}benzonitrile (D58, 592 mg, 0.0018 mol, 1 eq), 10% palladium on carbon (200 mg, 0.00018 mol, 0.1 eq), ammonium formate (375 mg, 0.0057 mol, 3.2 eq), and methanol (15 ml) (degassed with nitrogen) were combined and stirred for 1 hour. The catalyst was then filtered off, and the reaction evaporated, water and dichloromethane added and shaken. Separation and drying of the dichloromethane layer with sodium sulfate followed by evaporation yielded a crude product which was purified exactly as in Example 1 where A=H2O and B=acetonitrile to afford the title compound. MS (ESI): 301 [M+H]+

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe reaction evaporated
  3. additionwater and dichloromethane added
  4. stirringshaken
  5. customSeparation
  6. dry with materialdrying of the dichloromethane layer with sodium sulfate
  7. customfollowed by evaporation
  8. customyielded a crude product which
  9. customwas purified exactly as in Example 1 where A=H2O and B=acetonitrile

Sources & evidence

ORD record
ord-c50eef82c15a46b99394938d6b4ac216
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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