Isobutyric Acid → Isobutyric acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 1041910Notes

Reaction equation

HRID 1041910 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.CCN=C=NCCCN(C)C.Cl.Cl.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 6590Isobutyric AcidHCID 516892Sodium BicarbonateHCID 27960291-Hydroxybenzotriazole hydrateHCID 199167865-Fluoro-2-hydrazinylpyridineHCID 221413011-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride hydrochloride

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 EDCl HCl (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 (DCM/EtOAc 9/1 to 3/7) to give the title compound (0.42 g, 46%). LCMS (Method 8): 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 (DCM/EtOAc 9/1 to 3/7)

Sources & evidence

ORD record
ord-ea84c0ea6d1745678ce4a843ad17633e
Source dataset
uspto-grants-2013_10
Patent number
US08557797B2

Reaction notes

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