N-methylhydroxylamine hydrochloride → HCID 58424037, compound

HRID 1408721Notes

Reaction equation

HRID 1408721 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][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1)[CH2:13]/[C:12]/2=[N:30]\[C:31]#[N:32]>CO>[Br:8][C:9]1[CH:10]=[C:11]2[C:12]3([O:4][N:3]([CH3:2])[C:31]([NH2:32])=[N:30]3)[CH2:13][CH:14]([C:19]3[CH:20]=[CH:21][C:22]([O:25][C:26]([F:27])([F:28])[F:29])=[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 178511923HCID 178511923, compound

Product 1

HCID 58424037HCID 58424037, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methylhydroxylamine HCl salt (110 mg, 1.317 mmol) in anhydrous MeOH (15 mL) was added NaOMe (25 w % in MeOH, 0.23 mL, 1.02 mmol), followed by (E)-N-(6-bromo-2-(4-(trifluoromethoxy)phenyl)chroman-4-ylidene)cyanamide (540 mg, 1.32 mmol). After stirring for 10 min, the solvent was removed in vacuo. The residue was redissolved in DCM (20 mL). The mixture was filtered and the solvent was removed in vacuo, which was purified by preparative TLC to give 50 mg crude product of 6-bromo-2′-methyl-2-(4-(trifluoromethoxy)phenyl)-2′H-spiro[chroman-4,5′-[1,2,4]oxadiazol]-3′-amine (100 mg, 20%).

Workup

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

Sources & evidence

ORD record
ord-6f823981ea2247b2bdc52d27ec5b7f43
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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