N-methylhydroxylamine hydrochloride → HCID 58424307, compound

HRID 1408713Notes

Reaction equation

HRID 1408713 reaction equation
Cl.[CH3:2][NH:3][OH:4].[CH3:5][O-:6].[Na+].[Br:8][C:9]1[CH:10]=[C:11]2C(=[CH:17][CH:18]=1)O[CH:14]([C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)[CH2:13]/[C:12]/2=[N:25]\[C:26]#[N:27]>CO>[Br:8][C:9]1[CH:10]=[C:11]2[C:12]3([O:4][N:3]([CH3:2])[C:26]([NH2:27])=[N:25]3)[CH2:13][CH:14]([C:19]3[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=3)[O:6][C:5]2=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 10942334Sodium MethoxideHCID 178511925HCID 178511925, compound

Product 1

HCID 58424307HCID 58424307, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methylhydroxylamine HCl salt (76.9 mg, 0.92 mmol) in anhydrous MeOH (11 mL) was added NaOMe (25 w % in MeOH, 0.19 mL, 0.828 mmol), followed by (E)-N-(6-bromo-2-(pyridin-4-yl)chroman-4-ylidene)cyanamide (300 mg, 0.92 mmol), After stirring for 10 min, the solvent was removed in vacuo. The residue was dissolved in DCM (20 mL). The mixture was filtered, and the solvent was removed in vacuo to give a reside, which was purified by preparative TLC to give 6-bromo-2′-methyl-2-(pyridin-4-yl)-2′H-spiro[chroman-4,5′-[1,2,4]oxadiazol]-3′-amine (80 mg, 30%).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in DCM (20 mL)
  3. filtrationThe mixture was filtered
  4. customthe solvent was removed in vacuo
  5. customto give a reside, which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-09eda138f2344e5b8687d27d8fafb2f4
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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