Chlorosuccinimide → (4-chloro-2-methyl-5-pyridin-3-yl-2H-pyrazol-3-yl)-methylamine

HRID 1484717Notes

Reaction equation

HRID 1484717 reaction equation
[CH3:1][NH:2][C:3]1[N:4]([CH3:14])[N:5]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=1.[Cl:15]N1C(=O)CCC1=O>C(#N)C>[Cl:15][C:7]1[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:5][N:4]([CH3:14])[C:3]=1[NH:2][CH3:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 67499915methyl-(2-methyl-5-pyridin-3-yl-2H-pyrazol-3-yl)-amine

Product 1

HCID 67499720(4-chloro-2-methyl-5-pyridin-3-yl-2H-pyrazol-3-yl)-methylamineYield 24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl-(2-methyl-5-pyridin-3-yl-2H-pyrazol-3-yl)-amine (0.35 g, 1.8 mmol) and N-chlorosuccinimide (0.273 g, 2 mmol) was combined in acetonitrile (3 mL), stirred at room temperature for 30 minutes, concentrated under reduced pressure and purified using silica gel chromatography eluting with a gradient of EtOAc in hexanes to yield the title compound as a yellow oil (0.096 g, 23%): IR (thin film) 1581.6 cm−1; 1H NMR (400 MHz, CDCl3) δ 9.12 (d, J=1.5 Hz, 1H), 8.57 (dd, J=4.8, 1.3 Hz, 1H), 8.15 (ddd, J=7.8, 2.0, 2.0 Hz, 1H), 7.33 (dd, J=8.1, 5.1 Hz, 1H), 3.80 (s, 3H), 2.91 (d, J=5.8 Hz, 3H); ESIMS (m/z) 225.6 [M+2].

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified
  3. washeluting with a gradient of EtOAc in hexanes

Sources & evidence

ORD record
ord-52badb314c3a449f8d89584860051fca
Source dataset
uspto-grants-2016_08
Patent number
US09422278B2

Reaction notes

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