Formic Acid → HCID 58661553, compound

HRID 898698Notes

Reaction equation

HRID 898698 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]([NH:21][NH2:22])=[CH:16][C:17]=1[CH2:18][CH2:19][CH3:20])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:5].[CH:28](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]([CH2:18][CH2:19][CH3:20])=[CH:16][C:15]2[N:14]([CH:28]=[N:22][N:21]=2)[N:13]=1)=[O:5]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 58661545HCID 58661545, compound

Product 1

HCID 58661553HCID 58661553, compound

Procedure

A solution of 2,5-difluoro-N-(6-hydrazino-4-propyl-pyridazin-3-ylmethyl)-N-isobutyl-benzamide (78 mg, 0.21 mmol) in HCOOH (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) 9.07 (s, 0.2H), 9.00 (s, 0.8H), 7.87 (s, 0.8H), 7.78 (s, 0.2H), 6.96-7.13 (m, 3H), 4.91 (s, 1.6H), 4.62 (s, 0.4H), 3.13 (d, 2H), 2.71 (t, 1.6H), 2.40 (t, 0.4H), 2.09-2.13 (m, 0.2H), 1.92-2.00 (m, 0.8H) 1.74-1.83 (m, 1.6H), 1.48-1.55 (m, 0.4H), 1.09 (t, 2.4H), 1.00 (d, 1.2 H), 0.96 (t, 0.6H), 0.81 (d, 4.8H).

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-b549ed031f2d478b81e7d7445e90defb
Source dataset
uspto-grants-2008_04
Patent number
US07351826B2

Reaction notes

Loading…