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

HRID 1906786Notes

Reaction equation

HRID 1906786 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 ethyl acetate-hexane, giving 1.60 g of the desired product as light orange crystals, mp 146°-150° C.

Workup

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

Sources & evidence

ORD record
ord-9cbf97ee867b44c6b16054620370ddb0
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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