Ethylamine → HCID 66936229, compound

HRID 657905Notes

Reaction equation

HRID 657905 reaction equation
Cl.[CH3:2][C:3]1[C:8]([C:9]([O:11]C)=O)=[N:7][N:6]2[C:13]([NH:16][CH3:17])=[N:14][N:15]=[C:5]2[C:4]=1[CH3:18].[CH2:19]([NH2:21])[CH3:20]>CO>[CH2:19]([NH:21][C:9]([C:8]1[C:3]([CH3:2])=[C:4]([CH3:18])[C:5]2[N:6]([C:13]([NH:16][CH3:17])=[N:14][N:15]=2)[N:7]=1)=[O:11])[CH3:20]

Participants

4

Reactant 2

HCID 6341Ethylamine2×HCID 66936410HCID 66936410, compound

Product 1

HCID 66936229HCID 66936229, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 7,8-dimethyl-3-methylamino-[1,2,4]triazolo[4,3-b]pyridazine-6-carboxylate hydrochloride (W1.220; 1.3 g) was dissolved in methanol (30 ml), cooled to 0° C., slowly admixed dropwise with ethylamine (11.44 ml; 2 M in THF) and stirred at 0° C. for 6 h. Then four further equivalents ethylamine were added and the mixture was left to stand at RT over the weekend. Subsequently, the mixture was concentrated and purified using silica gel (40 g cartridge, dichloromethane/methanol gradient of 0-20% in 60 min). 1.12 g of the title compound were obtained. LC-MS rt: 0.81 min [M+H]+: 249.1 (met. b)

Workup

  1. waitthe mixture was left
  2. customto stand at RT over the weekend
  3. concentrationSubsequently, the mixture was concentrated
  4. custompurified
  5. customsilica gel (40 g cartridge, dichloromethane/methanol gradient of 0-20% in 60 min)

Sources & evidence

ORD record
ord-99043021b5a04ba8ad3f40073e172014
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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