Ethylamine → HCID 66936229, compound

HRID 532338Notes

Reaction equation

HRID 532338 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 of 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-e15a17f8ea1245a9964fa8a83229977d
Source dataset
uspto-grants-2014_10
Patent number
US08853206B2

Reaction notes

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