Methyl iodide → Methyl[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]carbamic acid, methyl ester

HRID 35624Notes

Reaction equation

HRID 35624 reaction equation
[CH3:1][C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:12]=[C:13]([NH:17][C:18](=[O:21])[O:19][CH3:20])[CH:14]=[CH:15][CH:16]=3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[H-].[Na+].CI.[C:26](=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:26][N:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]3[N:6]([C:2]([CH3:1])=[N:3][N:4]=3)[N:7]=2)[CH:12]=1)[C:18](=[O:21])[O:19][CH3:20]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 15595664[3-(3-Methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]carbamic acid, methyl ester

Product 1

HCID 15595667Methyl[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]carbamic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.27 g of [3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]carbamic acid, methyl ester, 100 ml of dry dimethylformamide and 0.129 g of sodium hydride was stirred under argon, for 30 minutes, then 0.31 ml of methyl iodide was added. This mixture was stirred for 2 hours, then poured into saturated aqueous sodium bicarbonate and extracted with dichloromethane. The extracts were combined, dried and evaporated. The residue was dissolved in dichloromethane:methanol (95:5) and filtered through a short plug of silica gel. The filtrate was concentrated and the resulting solid chromatographed on a column of 500 g of silica gel, eluting with dichloromethane:methanol (97:3). Fractions containing product were combined, evaporated and the solid recrystallized from dichloromethane-hexane, giving 0.92 g of the desired product as off-white crystals, mp 164°-166° C.

Workup

  1. stirringThis mixture was stirred for 2 hours
  2. extractionextracted with dichloromethane
  3. customdried
  4. customevaporated
  5. dissolutionThe residue was dissolved in dichloromethane:methanol (95:5)
  6. filtrationfiltered through a short plug of silica gel
  7. concentrationThe filtrate was concentrated
  8. customthe resulting solid chromatographed on a column of 500 g of silica gel
  9. washeluting with dichloromethane:methanol (97:3)
  10. additionFractions containing product
  11. customevaporated
  12. customthe solid recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-d39ee343ed9f48969bd63af4b9548a81
Source dataset
uspto-grants-1988_08
Patent number
US04767765

Reaction notes

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