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1,2-Dichloroethane → 5-Cyano-N-methoxy-N,2-dimethyl-6-oxo-4-p-tolyl-1,2,3,6-tetrahydropyridine-2-carboxamide

HRID 1629807
Notes
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Reaction equation

HRID 1629807 reaction equation
[C:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:13])([C:10]([OH:12])=O)[CH2:5][C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)#[N:2].[CH3:21][NH:22][O:23][CH3:24].C(Cl)CCl.CN1CCOCC1>C(Cl)Cl>[C:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:13])([C:10]([N:22]([O:23][CH3:24])[CH3:21])=[O:12])[CH2:5][C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 14232N,O-DimethylhydroxylamineHCID 866858995-Cyano-2-methyl-6-oxo-4-p-tolyl-1,2,3,6-tetrahydropyridine-2-carboxylic acid

Product 1

HCID 866859005-Cyano-N-methoxy-N,2-dimethyl-6-oxo-4-p-tolyl-1,2,3,6-tetrahydropyridine-2-carboxamideYield 31%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

Intermediate 108C (0.25 g, 0.925 mmol) was dissolved in DCM (15 mL) in a 25 mL 1 neck rb flask that was equipped with a magnetic stirrer and an Ar inlet. N,O-Dimethylhydroxylamine (0.062 g, 1.017 mmol), EDC (0.195 g, 1.017 mmol) and N-methylmorpholine (0.112 mL, 1.017 mmol) were added and the reaction mixture was stirred at rt overnight. The reaction solvent was removed under vacuum. The residue was dissolved in EtOAc (10 mL) and washed with water (5 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to a dark solid. The crude product was purified by silica gel chromatography (40 g silica gel, eluted with 0-100% EtOAc in hexanes) to give the desired product (0089 g, 31%) as a white solid. LCMS Anal. Calc'd for C17H19N3O3 313.3, found [M+H] 314.1. 1H NMR (500 MHz, CDCl3) δ 7.67 (d, J=8.3 Hz, 2H), 7.30 (d, J=8.0 Hz, 2H), 3.81 (s, 3H), 3.69-3.75 (m, 1H), 3.22 (s, 3H), 2.72 (d, J=17.6 Hz, 1H), 2.42 (s, 3H), 1.63 (s, 3H).

Workup

  1. customwas equipped with a magnetic stirrer
  2. customThe reaction solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in EtOAc (10 mL)
  4. washwashed with water (5 mL)
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated in vacuo to a dark solid
  7. customThe crude product was purified by silica gel chromatography (40 g silica gel, eluted with 0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-562fe7b00f7c48d7987efc00adadc548
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08791091B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes