HCID 69263789, compound → HCID 58661554, compound

HRID 898699Notes

Reaction equation

HRID 898699 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:3]=1[C:4]([N:6]([CH2:11][C:12]1[N:13]=[N:14][C:15](CCCNN)=[CH:16][CH:17]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:5]>CC(O)=O>[F:1][C:2]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:3]=1[C:4]([N:6]([CH2:7][CH:8]([CH3:10])[CH3:9])[CH2:11][C:12]1[C:17]([CH2:3][CH2:2][CH3:26])=[CH:16][C:15]2[N:14]([C:12]([CH3:11])=[N:13][N:14]=2)[N:13]=1)=[O:5]

Participants

3

Reactant 1

HCID 69263789HCID 69263789, compound

Product 1

HCID 58661554HCID 58661554, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2,5-difluoro-N-(6-hydrazinopropyl-pyridazin-3-ylmethyl)-N-isobutyl-benzamide (63 mg, 0.17 mmol) in HOAc (3 ml) is heated at 110° C. overnight. The solvent is removed in vacuo and to the residue is added EtOAc (10 ml) and saturated NaHCO3 aqueous solution (10 ml). The layers are separated and the aqueous layer is extracted with EtOAc (10 ml). The combined extracts are washed with brine (10 ml), dried (Na2SO4) and evaporated in vacuo. Preparative TLC separation of the residue with 5% MeOH in CH2Cl2 provides the title compound as a light yellow oil. 1H NMR (CDCl3) (mixture of rotamers) 7.79 (s, 0.75H), 7.71 (s, 0.25H), 6.95-7.12 (m, 3H), 4.91 (s, 1.5H), 4.62 (s, 0.5H), 3.17 (d, 2H), 2.81 (s, 0.75H), 2.79 (s, 2.25H), 2.69 (t, 1.5H), 2.39 (t, 0.5H), 2.06-2.17 (m, 0.25H), 1.91-2.01 (m, 0.75H), 1.72-1.82 (m, 1.5H), 1.45-1.55 (m, 0.5H), 1.08 (t, 2.25H), 1.00 (d, 4.5H), 0.93 (t, 0.75H), 0.82 (d, 1.5H).

Workup

  1. customThe solvent is removed in vacuo and to the residue
  2. additionis added EtOAc (10 ml) and saturated NaHCO3 aqueous solution (10 ml)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (10 ml)
  5. washThe combined extracts are washed with brine (10 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customPreparative TLC separation of the residue with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-84f7b1e3b78e4778a26a0230661099c5
Source dataset
uspto-grants-2008_04
Patent number
US07351826B2

Reaction notes

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