1,2-Dichloroethane → Isobutyric acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 1406683

Reaction equation

HRID 1406683 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[C:10](O)(=[O:14])[CH:11]([CH3:13])[CH3:12].C1C=C2N=NN(O)C2=CC=1.O.C(Cl)CCl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6590Isobutyric AcidHCID 516892Sodium BicarbonateHCID 27960291-Hydroxybenzotriazole hydrateHCID 199167865-Fluoro-2-hydrazinylpyridine

Product 1

HCID 66977821Isobutyric acid N'-(5-fluoro-pyridin-2-yl)-hydrazideYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-fluoro-2-hydrazinyl-pyridine (0.59 g, 4.65 mmol), isobutyric acid (528 mg, 6 mmol), and HOBt hydrate (153 mg, 1 mmol) in DCM (10 mL) was treated with EDC (1.15 g, 6 mmol). The reaction mixture was stirred at RT for 40 min, poured onto sat. aq. sodium bicarbonate (40 mL), extracted with four portions of DCM, dried (Na2SO4), evaporated and purified by FCC using 10-30% EtOAc/DCM to give the title compound (0.42 g, 46%). LCMS (method 2): Rt 2.46 min, m/z 198 [MH+].

Workup

  1. extractionextracted with four portions of DCM
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. custompurified by FCC

Sources & evidence

ORD record
ord-f64fbdcf1c55469ca59147b1d94fad71
Source dataset
uspto-grants-2014_12
Patent number
US08916708B2

Linked notes

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