Dimethylformamide → N-Methyl-N-[3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]propanamide

HRID 329618Notes

Reaction equation

HRID 329618 reaction equation
[N:1]1[N:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])[CH:13]=[CH:14][CH:15]=1)=[N:5]2.[H-].[Na+].[CH3:23]N(C)C=O.CI>O>[CH3:23][N:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:6]2[CH:7]=[CH:8][C:9]3[N:4]([CH:3]=[N:2][N:1]=3)[N:5]=2)[CH:11]=1)[C:17](=[O:20])[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 7532148HCID 7532148, compound

Product 1

HCID 15595655N-Methyl-N-[3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]propanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.58 g of N-[3-(1,2,4-triazolo(4,3-b]pyridazin-6-yl)phenyl]propanamide, 0.71 g of sodium hydride (50% in oil) and 200 ml of dimethylformamide was stirred under argon, for 1 hour. A 0.92 ml portion of methyl iodide was added and the mixture was stirred overnight. A 0.355 g portion of sodium hydride (50% in oil) and 0.46 ml of methyl iodide were added and stirring was continued overnight. The mixture was poured into 200 ml of water and extracted with 150 ml portions of dichloromethane. The extracts were combined dried and evaporated in vacuo. The residue was crystallized from ehtyl acetate-hexane, giving 1.60 g of the desired product as light orange crystals, mp 140°-150° C.

Workup

  1. stirringthe mixture was stirred overnight
  2. stirringstirring
  3. waitwas continued overnight
  4. extractionextracted with 150 ml portions of dichloromethane
  5. customThe extracts were combined dried
  6. customevaporated in vacuo
  7. customThe residue was crystallized from ehtyl acetate-hexane

Sources & evidence

ORD record
ord-e00407bd84b046d7a911b951b54f4150
Source dataset
uspto-grants-1990_01
Patent number
US04892873

Reaction notes

Loading…