Methanol → HCID 58424003, compound

HRID 2096592Notes

Reaction equation

HRID 2096592 reaction equation
Cl.[CH3:2][NH:3][OH:4].CO[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][CH:22]=[CH:21][N:20]=1)[CH2:13][C:12]2=[N:25][C:26]#[N:27].[CH3:28][OH:29]>>[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:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[O:29][C:28]2=[CH:17][CH:18]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 77906N-methylhydroxylamine hydrochlorideHCID 58424074HCID 58424074, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 58424003HCID 58424003, compoundYield 40%

Procedure

To a solution of N-methyl-hydroxylamine hydrochloride (31 mg, 0.31 mmol) in MeOH (4 mL) was added MeONa (0.06 mL, 25% (Wt.) in MeOH), followed by 6-bromo-2-pyridin-2-yl-chroman-4-ylidene-cyanamide (100 mg, 0.31 mmol). After stirred for 10 minutes, the solvent was removed in vacuo. The residue was purified by preparative TLC to give 6-bromo-2′-methyl-2-(pyridin-2-yl)-2′H-spiro[chroman-4,5′-[1,2,4]oxadiazol]-3′-amine (45 mg, 40%). 1H-NMR (MeOD): 2.13 (m, 1H), 2.48 (m, 1H), 3.08 (m, 3H), 5.32 (m, 1H), 6.86 (m, 1H), 7.36 (m, 2H), 7.51 (m, 1H), 7.68 (m, 1H), 7.90 (m, 1H), 8.52 (m, 1H.).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-6673c4b8010341ab9493922b34323614
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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