HCID 17393332, compound → HCID 57656461, compound

HRID 911634Notes

Reaction equation

HRID 911634 reaction equation
[CH2:1]([NH:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)C>[CH2:1]([NH:8][C:9]1[N:10]=[CH:11][C:12]([CH2:13][NH2:14])=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 17393332HCID 17393332, compound

Product 1

HCID 57656461HCID 57656461, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Stir 6-benzylamino-nicotinonitrile (680 mg, 3.3 mmol) and 10% Pd/C (Degussa type E101) vigorously in absolute ethanol (80 mL) under hydrogen at 25 psi for 1 h. Filter the solution through Celite® and concentrate in vacuo. Purify by chromatography on silica gel eluting sequentially with 2M ammonia in methanol/dichloromethane (4:96, 9:91) to give the title compound as a white solid (320 mg, 45%). MS (ES+) m/z: 214 (M+H)+.

Workup

  1. filtrationFilter the solution through Celite®
  2. concentrationconcentrate in vacuo
  3. customPurify by chromatography on silica gel eluting sequentially with 2M ammonia in methanol/dichloromethane (4:96, 9:91)

Sources & evidence

ORD record
ord-bdbb32bf338d47c58cb8e6e800ba0c76
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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