Ammonium formate → HCID 66756709, compound

HRID 855849Notes

Reaction equation

HRID 855849 reaction equation
C(OC(=O)[NH:10][C:11]1([CH3:25])[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[N:19][CH:20]=[C:21]([C:23]#[N:24])[CH:22]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)(C)C.[Pd]>[NH2:10][C:11]1([CH3:25])[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[N:19][CH:20]=[C:21]([C:23]#[N:24])[CH:22]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66756728HCID 66756728, compound

Product 1

HCID 66756709HCID 66756709, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of (5′-cyano-4-methyl-3,4,5,6-tetrahydro-2H-(1,3′)bipyridinyl-4-yl)-carbamic acid benzyl ester (0.051 g, 0.15 mmol) in isopropanol, (3.0 mL) at room temperature was added ammonium formate (0.050 g, 0.8 mmol) and 10% Pd/C (15 mg) under nitrogen. The reaction mixture was stirred at 90° C. for 18 hours, cooled, filtered through Celite and concentrated under reduced pressure to provide the titled compound. MS (CI) m/z 292 (M+1)+; 1H NMR (300 MHz, methanol-d4) δ ppm 8.48 (d, 1H), 8.18 (d, 1H), 7.65 (m, 1H), 3.49-3.36 (m, 2H), 3.32-3.36 (m, 2H), 1.73-1.61 (m, 4H), 1.20 (s, 3H).

Workup

  1. temperaturecooled
  2. filtrationfiltered through Celite
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfc23ba5a2f64829ba287fdd5d3635bd
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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