N-methylhydroxylamine hydrochloride → HCID 58423876, compound

HRID 2096594Notes

Reaction equation

HRID 2096594 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:20]=[N:21][CH:22]=[CH:23][CH:24]=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]=[N:21][CH: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 178511916HCID 178511916, compound

Product 1

HCID 58423876HCID 58423876, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methylhydroxylamine HCl salt (176 mg, 2.1 mmol) in anhydrous MeOH (15 mL) was added NaOMe (25% in MeOH (Wt. %), 0.47 mL, 1.89 mmol), followed by (E)-N-(6-bromo-2-(pyridine-3-yl)chroman-4-ylidene)cyanamide (687 mg, 2.1 mmol). After stirred for 10 mins, the solvent was removed in vacuo. The residue was redissolved in DCM (15 mL). The mixture was filtered, and the solvent was removed to give the residue, which was purified by preparative TLC to give 6-bromo-2′-methyl-2-(pyridine-3-yl)-2′H-spiro-[chroman-4,5′-[1,2,4]oxadiazol]-3′-amine (190 mg, 24%). 1H-NMR (MeOD): 2.18-2.25 (m, 1H), 2.39 (m, 1H), 3.09 (s, 3H), 5.34-5.38 (m, 1H), 6.81-6.86 (t, 1H), 7.37-7.40 (m, 1H), 7.45-7.55 (m, 1H), 7.62 (s, 1H), 7.97-7.99 (m, 1H), 8.52-8.54 (m, 1H), 8.66 (d, 1H).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was redissolved in DCM (15 mL)
  3. filtrationThe mixture was filtered
  4. customthe solvent was removed
  5. customto give the residue, which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-89e7ac4d91bc4489ac3819b40675c619
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

Loading…