2,2-dimethyl-N-(6-methyl-pyridazine-3-yl)-propionamide → N-(4-ethyl-6-methyl-pyridazin-3-yl)-2,2-dimethyl-propionamide

HRID 226028Notes

Reaction equation

HRID 226028 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6]1[N:7]=[N:8][C:9]([CH3:12])=[CH:10][CH:11]=1)=[O:4].[CH3:15][CH2:16][Mg+].[Br-]>>[CH2:15]([C:11]1[CH:10]=[C:9]([CH3:12])[N:8]=[N:7][C:6]=1[NH:5][C:3](=[O:4])[C:2]([CH3:14])([CH3:13])[CH3:1])[CH3:16]

Participants

3

Reactant 2

HCID 688407892,2-dimethyl-N-(6-methyl-pyridazine-3-yl)-propionamideHCID 178461630HCID 178461630, compound

Product 1

HCID 68858067N-(4-ethyl-6-methyl-pyridazin-3-yl)-2,2-dimethyl-propionamideYield 17.4%

Procedure

Using a procedure analogous to Example 17A, 2,2-dimethyl-N-(6-methyl-pyridazin-3-yl)-propionamide (4.18 g, 21.65 mmol) and 3.0 M solution of EtMgBr (36 mL, 108.29 mmol) give the title compound (0.83 g, 3.76 mmol, 17%). 1H NMR (CDCl3): δ 1.24 (t, J=7.5 Hz, 3H), 1.37 (s, 9H), 2.62 (q, J=7.5 Hz, 2H), 2.66 (s, 3H), 7.23 (s, 1H), 8.50 (s, 1H) ppm. ES-MS (m/z): calcd for C12H19N3O (M+H)+: 222.3. found: 222.1.

Sources & evidence

ORD record
ord-9b7727861e8f4303aebed6b926ac2790
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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