N-methylhydroxylamine hydrochloride → HCID 58424550, compound

HRID 2096512Notes

Reaction equation

HRID 2096512 reaction equation
Cl.[CH3:2][NH:3][OH:4].C[O-].[Na+].[C:8]([C:10]1[CH:11]=[C:12]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[O:22][CH:21]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:20]/[C:19]/3=[N:32]\[C:33]#[N:34])[CH:13]=[CH:14][CH:15]=1)#[N:9]>CO>[NH2:34][C:33]1[N:3]([CH3:2])[O:4][C:19]2([C:18]3[C:23](=[CH:24][CH:25]=[C:16]([C:12]4[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=4)[C:8]#[N:9])[CH:17]=3)[O:22][CH:21]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH2:20]2)[N:32]=1

Participants

5

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 10942334Sodium MethoxideHCID 178511917HCID 178511917, compound

Product 1

HCID 58424550HCID 58424550, compoundYield 3.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methylhydroxylamine HCl salt (17 mg, 0.2 mmol) in anhydrous MeOH (2 mL) was added NaOMe (25% in MeOH (Wt. %), 0.10 mL, 0.2 mmol), followed by (E)-N-(6-(3-cyanophenyl)-2-(pyridine-3-yl)chroman-4-ylidene)cyanamide (70 mg, 0.2 mmol). After stirring for 10 mins, the solvent was removed in vacuo. The resulting residue was redissolved in DCM (5 mL). The mixture was filtered, and the solvent was removed to give the residue, which was purified by preparative TLC and preparartive HPLC to give 3-(3′-amino-2′-methyl-2-(pyridine-3-yl)-2′H-spiro[chroman-4,5′-[1,2,4]oxadiazole]-6-yl)benzonitrile (2.5 mg, 3%). 1H-NMR (MeOD): 2.40-2.47 (t, 1H), 2.92-3.16 (m, 1H), 3.46 (s, 3H), 5.61-5.69 (m, 1H), 7.21 (m, 1H), 7.64-7.67 (m, 1H), 7.75 (d, 1H), 7.81-7.88 (m, 2H), 7.96-8.00 (t, 1H), 8.04-8.10 (t, 2H), 8.40 (m, 1H), 8.43 (m, 1H), 8.75 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-0260a1349bd04eb1acec797029d013f0
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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