Hydroxyamine hydrochloride → HCID 69308237, compound

HRID 860512Notes

Reaction equation

HRID 860512 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-b8857a6358e64a4a9d6421dae4f33b4e
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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