N-methylhydroxylamine hydrochloride → HCID 58424768, compound

HRID 2096529Notes

Reaction equation

HRID 2096529 reaction equation
Cl.[CH3:2][NH:3][OH:4].CO[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:31]=[CH:30][CH:29]=[CH:28][N:27]=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:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH2:20]2)[N:32]=1

Participants

5

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 178418582HCID 178418582, compoundHCID 178511907HCID 178511907, compound

Product 1

HCID 58424768HCID 58424768, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-methyl-hydroxylamine hydrochloride (14 mg, 0.14 mmol) in MeOH (4 mL) was added MeONa (0.03 mL, 25% (Wt.) in MeOH), followed (Z)—N-(6-(3-cyanophenyl)-2-(pyridin-2-yl)chroman-4-ylidene)cyanamide (50 mg, crude). After stirring for 10 minutes, the solvent was removed in vacuo to give a residue. The residue was purified by preparative TLC to give 3-(3′-amino-2′-methyl-2-(pyridin-2-yl)-2′H-spiro[chroman-4,5′-[1,2,4]oxadiazole]-6-yl)benzonitrile (4.3 mg, 8%). 1H-NMR (MeOD): 2.11 (m, 1H), 2.51 (m, 1H), 3.02 (s, 2H), 3.28 (s, 1H), 4.12 (m, 1H), 5.32 (m, 1H), 6.97 (m, 1H), 7.32 (m, 1H), 7.55 (m, 5H), 7.82 (m, 3H), 8.46 (m, 1H).

Workup

  1. customthe solvent was removed in vacuo
  2. customto give a residue
  3. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-68fca7906b5149d28dcba865afb73276
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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