Dimethylformamide → 6-chloro-N-(3-methylbutyl)pyridazine-3-carboxamide

HRID 2056409Notes

Reaction equation

HRID 2056409 reaction equation
O.O=[C:3]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=O)[CH:5]=[CH:4]1.CN(C)C=O.S(Cl)([Cl:19])=O.[CH3:21][CH:22]([CH3:26])[CH2:23][CH2:24][NH2:25]>C(Cl)(Cl)Cl.ClCCl.C(N(CC)CC)C>[CH3:21][CH:22]([CH3:26])[CH2:23][CH2:24][NH:25][C:9]([C:6]1[N:7]=[N:8][C:3]([Cl:19])=[CH:4][CH:5]=1)=[O:11]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7894IsoamylamineHCID 24386Thionyl ChlorideHCID 27746516-Hydroxy-3-pyridazinecarboxylic acid monohydrate

Product 1

HCID 167337866-chloro-N-(3-methylbutyl)pyridazine-3-carboxamideYield 98%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

The mixture of 6-oxo-1,6-dihydropyridazine-3-carboxylic acid monohydrate (3.16 g; 20.0 mmol), dimethylformamide (0.5 mL) and thionyl chloride (5-7 mL) in chloroform (70 mL) was kept at 50-60° C. overnight. The reaction mixture was evaporated in vacuo to dryness. The solid residue was dissolved in dichloromethane (70 mL) and added dropwise to the mixture of 3-methylbutylamine (30 mmol, 2.7 mL) and triethylamine (5 mL) in dichloromethane (150 mL) at ambient temperature. The mixture was stirred for 30 min, washed sequentially with 10% HCl solution, saturated NaHCO3 and water, and then dried over MgSO4. The final compound was isolated by recrystallization from ether:hexanes (5:1) (19.76 mmol). Yield: 98%.

Workup

  1. customThe reaction mixture was evaporated in vacuo to dryness
  2. dissolutionThe solid residue was dissolved in dichloromethane (70 mL)
  3. washwashed sequentially with 10% HCl solution, saturated NaHCO3 and water
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-b74c73244b564108b4a64dce612b1fc3
Source dataset
uspto-grants-2008_02
Patent number
US07335658B2

Reaction notes

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