2-Chloro-4-cyanopyridine → HCID 67398920, compound

HRID 2355599Notes

Reaction equation

HRID 2355599 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([NH2:23])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>CC(N(C)C)=O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:2]2[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][N:9]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 5686382-Chloro-4-cyanopyridineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 67398920HCID 67398920, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 2-chloro-isonicotinonitrile (2.00 g, 14.43 mmol, 1.0 equiv; commercially available) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (3.18 g, 15.88 mmol, 1.1 equiv; commercially available) in DMAc (10 mL) was heated by microwave irradiation to 150° C. for 30 min. The solvent was evaporated under reduced pressure and the crude material purified with column chromatography on silica eluting with heptane/ethyl acetate (1:1) to yield 0.30 g (7%) of the title compound. 1H NMR (300 MHz, CDCl3): δ1.25-1.42 (m, 2H), 1.43 (s, 9H), 1.93-1.97 (m, 2H), 2.83-2.93 (m, 2H), 3.71-3.81 (m, 1H), 3.97-4.02 (m, 2H), 4.77 (d, J=8.1 Hz, 1H), 6.51 (s, 1H), 6.66 (d, J=5.2 Hz, 1H), 8.11 (d, J=5.2 Hz, 1H). MS (ISP): 303.0 [M+H]+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude material purified with column chromatography on silica eluting with heptane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-4e6a5994d7ba46e9b9c6ddb7beab0491
Source dataset
uspto-grants-2010_07
Patent number
US07754744B2

Reaction notes

Loading…