Hydroxyamine hydrochloride → HCID 69308237, compound

HRID 2250657Notes

Reaction equation

HRID 2250657 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[N:10]([C:22]([CH:25]=O)=[CH:23][CH:24]=3)[N:11]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:13]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1.Cl.[NH2:28]O.C([O-])=O.[Na+]>C(O)=O>[C:25]([C:22]1[N:10]2[N:11]=[C:12]([CH:19]([CH3:20])[CH3:21])[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9]2=[CH:24][CH:23]=1)#[N:28]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 86597480HCID 86597480, compound

Product 1

HCID 69308237HCID 69308237, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of ethyl 4-(4-fluorophenyl)-7-formyl-2-isopropylpyrrolo[1,2-b]pyridazine-3-carboxylate (200 mg, 0.564 mmol), hydroxylamine hydrochloride (51.0 mg, 0.734 mmol), and sodium formate (69.1 mg, 1.02 mmol) in formic acid (2 mL) were refluxed for 2 h. The mixture was evaporated to give a green gum. The gum was partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate (5 mL). The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated to give a green gum. Flash silica gel column chromatography eluting with ethyl acetate-hexane=1-10 to 1-8 gave ethyl 7-cyano-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazine-3-carboxylate as an yellow crystal (144 mg, 72.6%).

Workup

  1. customThe mixture was evaporated
  2. customto give a green gum
  3. customThe gum was partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate (5 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto give a green gum
  8. washFlash silica gel column chromatography eluting with ethyl acetate-hexane=1-10 to 1-8

Sources & evidence

ORD record
ord-c4856780e9e34026a40200847eeec175
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

Loading…