Pyridine → 2-(3-bromo-quinolin-6-yloxy)-N-(2-butoxyimino-1,1-dimethyl-ethyl)-2-methylsulfanyl-acetamide

HRID 1892041Notes

Reaction equation

HRID 1892041 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH:13]([S:22][CH3:23])[C:14]([NH:16][C:17]([CH3:21])([CH3:20])[CH:18]=O)=[O:15])=[CH:7][CH:6]=2.N1C=CC=CC=1.Cl.[CH2:31]([O:35][NH2:36])[CH2:32][CH2:33][CH3:34].C([O-])(O)=O.[Na+]>CO.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH:13]([S:22][CH3:23])[C:14]([NH:16][C:17]([CH3:21])([CH3:20])[CH:18]=[N:36][O:35][CH2:31][CH2:32][CH2:33][CH3:34])=[O:15])=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 12283956O-Butylhydroxylamine HydrochlorideHCID 866480202-(3-bromo-quinolin-6-yloxy)-N-(1,1-dimethyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide

Product 1

HCID 866480212-(3-bromo-quinolin-6-yloxy)-N-(2-butoxyimino-1,1-dimethyl-ethyl)-2-methylsulfanyl-acetamideYield 97.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(3-Bromo-quinolin-6-yloxy)-N-(1,1-dimethyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide (0.1 g) from Stage 2, Step 2 above, pyridine (0.022 ml) and O-n-butyl-hydroxylamine hydrochloride (0.035 g) in methanol (5 ml) were stirred at rt for 3 hours. The reaction mixture was diluted with ethyl acetate and poured onto sat. NaHCO3 (30 ml). The two phases were separated and the aqueous layer was extracted with ethyl acetate (3×50 ml). The organic layers were combined, dried over magnesium sulphate, filtered and evaporated. The residue was purified by column chromatography (heptane/ethyl acetate 3:1) to give 2-(3-bromo-quinolin-6-yloxy)-N-(2-butoxyimino-1,1-dimethyl-ethyl)-2-methylsulfanyl-acetamide as white solid (0.115 g). 1H NMR (CDCl3) δ ppm: 8.81 (1H, d); 8.24 (1H, d); 8.04 (1H, d); 7.71 (1H, s); 7.45 (1H, dd); 7.39 (1H, s); 7.17 (1H, d); 5.64 (1H, s); 4.08 (2H, t); 2.19 (3H, s); 1.68-1.58 (8H, m); 1.45-1.36 (2H, m), 0.94 (3H, t).

Workup

  1. customThe two phases were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×50 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (heptane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-d8a948508d0f494f9fda086093531339
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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