4-Methylmorpholine → N-methoxy-N-methyl-3'-nitro-3,6-dihydro-2H-1,2'-bipyridine-4-carboxamide

HRID 1896019Notes

Reaction equation

HRID 1896019 reaction equation
[N+:1]([C:4]1[C:5]([N:10]2[CH2:15][CH:14]=[C:13]([C:16]([OH:18])=O)[CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-].CN1CCOCC1.Cl.[CH3:45][NH:46][O:47][CH3:48]>CO>[CH3:48][O:47][N:46]([CH3:45])[C:16]([C:13]1[CH2:12][CH2:11][N:10]([C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH2:15][CH:14]=1)=[O:18]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 58319495HCID 58319495, compound

Product 1

HCID 86627348N-methoxy-N-methyl-3'-nitro-3,6-dihydro-2H-1,2'-bipyridine-4-carboxamideYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Compound 260a (100 mg, 0.40 mmol) in methanol (10 mL) stirred at r.t., was added DMT-MM (4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, 142 mg, 0.52 mmol), N-methylmorpholine (88.4 μL, 0.81 mmol) and N,O-dimethylhydroxylamine hydrochloride (60 mg, 0.615 mmol). The reaction mixture was stirred at r.t. for 3 h. The solvent was evaporated to dryness in vacuo. The residue was diluted with aq. 1N NaOH and dichloromethane. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether 60:40) affording the title product (90 mg).

Workup

  1. customThe solvent was evaporated to dryness in vacuo
  2. additionThe residue was diluted with aq. 1N NaOH and dichloromethane
  3. washThe combined organic layers were washed with brine
  4. customdried on Na2SO4
  5. customevaporated to dryness in vacuo
  6. customto afford a residue, which
  7. customwas purified by flash chromatography (EtOAc—Petroleum Ether 60:40)

Sources & evidence

ORD record
ord-43a7822292d84ef0abe015b481a05c90
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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