Piperidine → N-{6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}glycinamide

HRID 1504873Notes

Reaction equation

HRID 1504873 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10](=[O:30])[CH2:11][NH:12]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)=[CH:5][C:4]=1[NH:31][C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[N:33]=1)#[N:2].N1CCCCC1>CN(C=O)C>[C:1]([C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10](=[O:30])[CH2:11][NH2:12])=[CH:5][C:4]=1[NH:31][C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[N:33]=1)#[N:2]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 867317419H-fluoren-9-ylmethyl [2-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}amino)-2-oxoethyl]carbamate

Product 1

HCID 86731742N-{6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}glycinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 9H-fluoren-9-ylmethyl [2-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}amino)-2-oxoethyl]carbamate (120 mg, 0.23 mmol) in DMF (1.8 mL) was added piperidine (394 mg, 4.63 mmol). After 1 hour, the reaction mixture was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (0-70% ethyl acetate/hexanes, linear gradient, followed by 0-12% methanol/dichloromethane, linear gradient) to afford N-{6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}glycinamide. MS ESI calc'd for C15H17N6O [M+H]+ 297. found 297. 1H NMR (500 MHz, DMSO-d6) δ 9.09 (s, 1H), 8.85 (d, J=2.1 Hz, 1H), 8.43 (d, J=2.1 Hz, 1H), 6.64 (s, 1H), 6.61 (s, 1H), 3.31 (s, 2H), 2.29 (s, 3H), 2.21 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel (0-70% ethyl acetate/hexanes, linear gradient, followed by 0-12% methanol/dichloromethane, linear gradient)

Sources & evidence

ORD record
ord-1e304f0676bf4feeb99d0b9098955fcc
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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