N-methylhydroxylamine hydrochloride → 6-bromo-2'-methyl-2-(tetrahydro-2H-pyran-3-yl)-2'H-spiro[chroman-4,5'-[1,2,4]oxadiazol]-3'-amine

HRID 1408690Notes

Reaction equation

HRID 1408690 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]([CH:19]1[CH2:24][CH2:23][CH2:22][O:21][CH2:20]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]([CH:19]3[CH2:24][CH2:23][CH2:22][O:21][CH2:20]3)[O:6][C:5]2=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 10942334Sodium MethoxideHCID 178511922HCID 178511922, compound

Product 1

HCID 584238486-bromo-2'-methyl-2-(tetrahydro-2H-pyran-3-yl)-2'H-spiro[chroman-4,5'-[1,2,4]oxadiazol]-3'-amineYield 10%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methylhydroxylamine HCl salt (75 mg, 0.9 mmol) in anhydrous MeOH (10 mL) was added NaOMe (25 w % in MeOH, 0.13 mL), followed by (E)-N-(6-bromo-2-(tetrahydro-2H-pyran-3-yl)chroman-4-ylidene)cyanamide (300 mg, 0.9 mmol). After stirring for 10 min, the solvent was removed in vacuo. The residue was redissolved in DCM (20 mL). The mixture was filter, and the solvent was removed in vacuo. The resulting residue was purified by preparative TLC to give 20 mg of 6-bromo-2′-methyl-2-(tetrahydro-2H-pyran-3-yl)-2′H-spiro[chroman-4,5′-[1,2,4]oxadiazol]-3′-amine (50 mg, 10%).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was redissolved in DCM (20 mL)
  3. filtrationThe mixture was filter
  4. customthe solvent was removed in vacuo
  5. customThe resulting residue was purified by preparative TLC

Sources & evidence

ORD record
ord-5c260bdb56714cc1950c96b199a14471
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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