Dimethylcarbamoyl Chloride → 2-(5-Fluoropyridin-2-yl)-N,N-dimethylhydrazine carboxamide

HRID 2282480Notes

Reaction equation

HRID 2282480 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[CH3:10][N:11]([CH3:15])[C:12](Cl)=[O:13].CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:12]([N:11]([CH3:15])[CH3:10])=[O:13])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 199167865-Fluoro-2-hydrazinylpyridine

Product 1

HCID 866870622-(5-Fluoropyridin-2-yl)-N,N-dimethylhydrazine carboxamideYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (5-fluoro-pyridin-2-yl)-hydrazine (500 mg, 3.93 mmol), dimethylcarbamyl chloride (505 mg, 4.72 mmol) and DIPEA (1.01 g, 7.86 mmol) in DCM (20 mL) was stirred at reflux for 16 h. The reaction mixture was applied to an SCX-2 cartridge (25 g) and washed with MeOH. The product was eluted with 2M NH3 in MeOH; concentration in vacuo and then trituration with diethyl ether gave the title compound (600 mg, 77%). 1H NMR (400 MHz, CDCl3): 2.99 (6H, s), 6.46 (2H, m), 6.75 (1H, dd, J 9.1, 3.5), 7.22-7.32 (1H, m), 8.03 (1H, d, J 2.7).

Workup

  1. temperatureat reflux for 16 h
  2. washwashed with MeOH
  3. washThe product was eluted with 2M NH3 in MeOH
  4. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-dcee64d2f4b0467e80f66edfc6beda5a
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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