Aminopyridazine → HCID 69937058, compound

HRID 1623751Notes

Reaction equation

HRID 1623751 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[N:20]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([NH:25][C:21]1[N:20]=[N:19][CH:24]=[CH:23][CH:22]=1)=[O:9]

Participants

4

Reactant 2

HCID 230373AminopyridazineHCID 24613572-(Benzyloxy)-5-bromobenzoic acid

Product 1

HCID 69937058HCID 69937058, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Solid 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5, method C; 200 mg, 0.651 mmol) was added to a stirred suspension of CD (106 mg, 0.651 mmol) in THF (6 ml) under nitrogen at 20° C. The reaction mixture was stirred at room temperature for 10 min and pyridazin-3-amine (61.9 mg, 0.651 mmol) was added dropwise. After refluxing for 14 h, the reaction mixture was concentrated to obtain crude product. The crude product was purified by silica gel chromatography, eluting with hexane:ethyl acetate (4:1) to yield the title compound. 183 mg.

Workup

  1. temperatureAfter refluxing for 14 h
  2. concentrationthe reaction mixture was concentrated
  3. customto obtain crude product
  4. customThe crude product was purified by silica gel chromatography
  5. washeluting with hexane:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-764528f7e49e418f9d5fdad637329017
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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